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Bromoacetate

Q: Are there different variations or types of Bromoacetate that researchers should be aware of?

Yes, there are several different variations of Bromoacetate that researchers may encounter, such as different salt forms (e.g., sodium Bromoacetate, potassium Bromoacetate) or Bromoacetate derivatives with additional functional groups. It's important to carefully select the appropriate Bromoacetate form for your specific application to ensure optimal results.

Bromoacetate is a chemical compound with the formula CH2BrCOO-, commonly used in scientific research.
It is a versatile reagent employed in various chemical reactions, including nucleophilic substitution, alkylation, and ester formation.
Bromoacetate is particularly useful in the synthesis of organic compounds and the modification of biomolecules.
Reserchers rely on optimized protocols and high-quality products to ensure reproducible and effiecient Bromoacetate-based experiments.
PubCompare.ai's AI-driven comparisons of literature, preprints, and patents can help identify the most reliable and efficient methods for your Bromoacetate research needs.

Most cited protocols related to «Bromoacetate»

Synthesis and Characterization of Gadolinium Contrast Agent

Unless noted, materials and solvents were purchased from Sigma-Aldrich Chemical Co. (St. Louis, MO) and used without further purification. GdCl₃·6H₂O and 1,4,7,10-tetraazacyclododecane (cyclen) were purchased from Strem Chemicals (Newburyport, MA) and used without further purification. Unless noted, all reactions were performed under a nitrogen atmosphere. THF, acetonitrile, and dichloromethane were purified using a Glass Contour Solvent system. Deionized water was obtained from a Millipore Q-Guard System equipped with a quantum Ex cartridge (Billerica, MA). Thin-layer chromatography (TLC) was performed on EMD 60F 254 silca gel plates. Visualization of compounds was accomplished using either an iodoplatinate or UV light. Standard grade 60 Å 230–400 mesh silca gel (Sorbent Technologies) was used for flash column chromatography.
¹H and ¹³C NMR spectra were obtained on a Bruker 500 MHz Avance III NMR Spectrometer or a Varian Inova 400 MHz NMR Spectrometer with deuterated solvent as noted. Electrospray ionization mass spectrometry (ESI-MS) spectra were taken on a Varian 1200 L single-quadrupole mass spectrometer. High resolution mass spectrometry data was aquired on an Agilent 6210 LC-TOF (ESI, APCI, APPI). Analytical reverse-phase HPLC-MS was performed on a Varian Prostar 500 system with a Waters 4.6 × 250 mm 5 μM Atlantis C18 column. This system is equipped with a Varian 380 LC ELSD system, a Varian 363 fluorescence detector, and a Varian 335 UV-Vis detector. Preparative runs were performed on a Water 19 × 250 mm Atlantis C18 Column. The mobile phases consisted of Millipore water (A) and HPLC-grade acetonitrile (B). HPLC method 1: 0–5 min 100% A, 5–24:08 min 57.5% A, 24:08–30 min 0% A, 30–35 min 0% A, 35–40 min 100% A.
Determination of r₁ was accomplished using a Bruker minispec 60 MHz (1.41 T) magnet and a Varian Inova 400 MHz (9.4 T) NMR Spectrometer. At 1.41 T the T₁ relaxation times were determined using an inversion recovery method while at 9.4 T a saturation recovery method was used. The saturation recovery method utilized a 2 second presaturation pulse centered on the water frequency. All measurements were done at 37 °C at an approximate 1 mM concentration of CA in 10 mM DPBS purchased from Invitrogen.
NMRD measurements were performed with a Stelar Spinmaster FFC-2000-1T fast field cycling relaxometer in the 0.01–40 MHz proton Larmor frequency range at 298 and 310 K. Standard field cycling protocol was used. Longitudinal water proton relaxation rates were obtained with an error smaller than 1%. Proton nuclear magnetic relaxation dispersion (NMRD) profiles were obtained by plotting proton relaxation rates as a function of applied magnetic field after subtraction of the diamagnetic contribution of buffer alone and normalization to 1 mM Gd(III) concentration.
(6) 1-azido-3-chloropropan-2-ol was synthesized as described by Ingham et al with the following modifications.⁶³ Diethyl ether was used in the place of dichloromethane in the procedure. The final product was not distilled as in the literature procedure but simply extracted into ether and evaporated. The product was used directly in subsequent reactions. Caution: Safe handling procedures for perchlorates and small molecule azides should be reviewed before performing this reaction, as there is a danger of explosion if heat, friction, or shock is applied.
Tri-tert-butyl 2,2′,2″-(1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate hydrobromide (trist-butyl-DO3A HBr) was synthesized according to the procedure of Oskar with the following modifications.⁶⁴ To a 500 mL RB flask was added 10.279 grams (59.8 mmoles) of cyclen to this was added 14.8405 grams (179.2 mmoles) of NaOAc. The solids were dissolved in 180 mL of dimethylacetamide (DMA). The reaction was cooled to 0 °C with ice and 26.5 mL (179.3 mmol) of tert-butyl bromoacetate dissolved in 70 mL of DMA was added drop wise over 40 minutes at 0 °C. The reaction was allowed to warm to RT and stirred for two days and was poured into a solution of 16.6 grams of KBr in 1000 mL of H₂O. The solution was brought to a basic pH with 17.7g (3.5 eq) of NaHCO₃. (Caution: A large amount of gas is produced.) Add 10 mL of ether to initiate precipitation of the HBr salt of tris-t-butyl-DO3A. The final white to off white powder was filtered and dried under vacuum to give a yield of 21.4976 grams (60% yield). ¹H NMR (500 MHz, CDCl₃) δ 3.56 – 2.57 (m, 21H), 1.46 (d, J = 3.6 Hz, 27H). ¹³C NMR (126 MHz, CDCl₃) δ 170.53, 169.63, 81.86, 81.71, 77.29, 77.04, 76.78, 58.22, 51.31, 51.12, 49.14, 47.53, 28.23, 28.19, 28.03, 0.00.

Mastarone D.J., Harrison V.S., Eckermann A.L., Parigi G., Luchinat C, & Meade T.J. (2011). A Modular System for the Synthesis of Multiplexed Magnetic Resonance Probes. Journal of the American Chemical Society, 133(14), 5329-5337.

Publication 2011

Synthesis of Polyethylene Glycol-Based Compounds

General method A. PEG (1 eq.) was solubilised in dioxane anhydrous and NaH (2 eq.) was added under stirring. The resulting mixture was stirred at r.t. for 3h. The mixture was cooled down to 0 °C using ice bath and tert-butylbromo acetate (2 eq.) was added drop by drop. The resulting mixture was stirred at r.t O/N. The precipitate was filtered off and the organic phase evaporated to dryness. The resulting oil was taken up with ethyl acetate, washed with water, dried over MgSO₄ and evaporated to dryness. The resulting oil was purified by column chromatography using a gradient of ethyl acetate from 50% to 100% v/v in heptane.
General method B. tert-butyl esters 1, 2, 3 or 12 were dissolved in a solution of 50% v/v trifluroacetic acid in DCM. The resulting solution was stirred for 1 h or until complete conversion of starting material. The solvent was removed under high vacuum. The resulting carboxylic acid was used as crude in the next step without any further purification. To a solution of carboxylic acid in 1 ml DMF were added HATU (1 eq.) and HOBT (1 eq.) and the pH of the reaction mixture was adjusted to > 9 by addition of DIPEA (3 eq.). The resulting solution was stirred at room temperature for 5 min and then amine 7 or 8 was added. The mixture was stirred at room temperature until no presence of the starting materials was detected by LC-MS. Water was added and the mixture was extracted with ethyl acetate (×3). The combined organic phases were washed with brine (×2), dried over MgSO₄ and evaporated under reduced pressure to give the corresponding crude, which was purified by HPLC using a gradient of 20% to 95% v/v acetonitrile in 0.1% aqueous solution of ammonia to yield the desired compound.
di‐tert‐butyl 3, 6, 9, 12 – tetraoxatetradecanedioate (1)

Following general method A, from triethylene glycol (1.125 g, 1 ml, 7.49 mmol, 1 eq.) in 10 ml of dioxane, NaH 60% in mineral oil (595.75 mg, 14.9 mmol, 2 eq.) and tert-Butyl bromoacetate (2.905 g, 2.19 ml, 14.9 mmol, 2 eq.), compound 1 was obtained as an oil after high vacuum. Yield: 538 mg, 1.42 mmol (19%). ¹H NMR (500 MHz, CDCl₃): δ 3.81 (s, 4H), 3.51–3.46 (m, 12H), 1.26 (s,18H). ¹³C NMR (126 MHz, CDCl₃): δ 169.1, 80.9, 70.1, 70.0, 68.5, 27.5. Analytical data matched those previously reported^{73 (link)}.
di‐tert‐butyl 3,6,9,12,15-pentaoxaheptadecanedioate (2)

Following general method A, from tetrathylene glycol (1.125 g, 1 ml, 5.49 mmol, 1 eq.) in 10 ml of dioxane, NaH 60% in mineral oil (463 mg, 11.5 mmol, 2 eq.) and tert-Butyl bromoacetate (2.25 g, 1.7 ml, 11.5 mmol, 2 eq.), compound 2 was obtained as an oil after high vacuum. Yield: 500 mg, 1.18 mmol (10%). ¹H NMR (500 MHz, CDCl₃): δ 3.86 (s, 4H), 3.55–3.49 (m, 16H), 1.31 (s, 9H). Analytical data matched those previously reported^{73 (link)}.
di‐tert‐butyl 3,6,9,12,15,18-hexaoxaicosanedioate (3)

Following general method A, from pentaethylene glycol (1.126 g, 1 ml, 4.72 mmol, 1 eq.) in 10 ml of dioxane, NaH 60% in mineral oil (377 mg, 9.45 mmol, 2 eq.) and tert-Butyl bromoacetate (1.872 g, 1.7 ml, 11.5 mmol, 2 eq.), compound 3 was obtained as an oil after high vacuum. Yield: 300 mg, 0,641 mmol (14%). ¹H NMR (400 MHz, CDCl₃): δ 3.94 (s, 4H), 3.66–3.56 (m, 20H), 1.40 (s, 18H). Analytical data matched those previously reported^{73 (link)}.
N¹,N¹⁴-bis((S)-1-((2S,4R)-4-hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)-3,6,9,12-tetraoxatetradecanediamide (CM09)

Following general method B, from compound 1 (6.80 mg, 0.018 mmol, 1 eq.), compound 7 (20 mg, 0.045 mmol, 2.5 eq.), HATU (17 mg, 0.045 mmol, 2.5 eq), HOAT (6.12, 0.045 mmol, 2.5 mmol) and DIPEA (6.98 mg, 0.054 mmol, 3 eq) compound CM09 was obtained as a white solid. Yield: 8 mg, 0.007 mmol (40%). ¹H NMR (400 MHz, CDCl₃): δ 8.61 (s, 2H), 7.48–7.45 (m, 2H), 7.31–7.27 (m, 8H), 7.23 (d, J = 10.2 Hz, 2H), 4.64–4.59 (m, 2H), 4.52–4.46 (m, 4H), 4.41–4.38 (m, 2H), 4.31–4.25 (m, 2H), 4.01–3.94 (m, 4H), 3.82 (d, J = 15.7 Hz, 2H), 3.62–3.52 (m, 12H), 2.45 (s, 6H), 2.42–2.34 (m, 2H), 2.12–2.06 (m, 2H), 1.19 (s, 2H), 0.89 (s, 18H); ¹³C NMR (101 MHz, CDCl₃): δ 170.2, 169.9, 169.6, 149.3, 147.5, 137.3, 130.6, 129.9, 128.4, 127.1, 69.9, 69.5, 69.3, 69.1, 57.6, 56.1, 55.9, 42.2, 35.5, 34.6, 25.4, 15.1. HRMS (ESI) m/z: [M + H]⁺ calculated for: C₅₄H₇₄N₈O₁₂S₂: 1090.49; observed: 1091.5093.
N¹,N¹⁷-bis((S)-1-((2S,4R)-4-hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)-3,6,9,12,15-pentaoxaheptadecanediamide (CM10)

Following general method B, from compound 2 (7.60 mg, 0.018 mmol, 1 eq.), compound 7 (20 mg, 0.045 mmol, 2.5 eq.), HATU (17 mg, 0.045 mmol, 2.5 eq), HOAT (6.12, 0.045 mmol, 2.5 mmol) and DIPEA (6.98 mg, 0.054 mmol, 3 eq) compound CM10 was obtained as a white solid. Yield: 6 mg, 0.005 mmol (30%). ¹H NMR (500 MHz, CDCl₃): δ p.p.m., 7.58–7.55 (m, 2H), 7.35–7.30 (m, 10H), 4.72–4.67 (m, 2H), 4.57–4.47 (m, 6H), 4.38–4.33 (m, 2H), 4.15–3.91 (m, 8H), 3.68–3.56 (m, 20H), 2.51 (s, 6H), 2.45–2.38 (m, 2H), 2.20–2.14 (m, 2H), 0.95 (s, 18H). ¹³C NMR (126 MHz, CDCl₃): δ 170.3, 169.8, 169.6, 149.6, 146.9, 137.5, 129.5, 128.47, 128.40, 127.1, 70.0, 69.56, 69.52, 69.5, 69.2, 69.1, 57.7, 56.03, 55.98, 42.1, 35.6, 34.6, 25.4, 14.8. HRMS (ESI)m/z: [M + H]⁺ calculated for: C₅₆H₇₈N₈O₁₃S₂: 1134.51; observed: 1135.5538.
N¹,N²⁰-bis((S)-1-((2S,4R)-4-hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)-3,6,9,12,15,18-hexaoxaicosanediamide (CM11)

Following general method B, from compound 3 (8.39 mg, 0.018 mmol, 1 eq.), compound 7 (20 mg, 0.045 mmol, 2.5 eq.), HATU (17 mg, 0.045 mmol, 2.5 eq), HOAT (6.12, 0.045 mmol, 2.5 mmol), DIPEA (6.98 mg, 0.054 mmol, 3 eq) compound CM11 was obtained as a white solid. Yield: 11.74 mg, 0.0099 mmol (55%). ¹H NMR (400 MHz, CDCl₃): δ 8.61 (s, 2H), 7.41–7.38 (m, 2H), 7.29 (t, J = 7.6 Hz, 10H), 4.66–4.61 (m, 2H), 4.49–4.41 (m, 6H), 4.35–4.29 (m, 2H), 3.98–3.91 (m, 6H), 3.62–3.50 (m, 24H), 2.45 (s, 6H), 2.42–2.35 (m, 2H), 2.11–2.06 (m, 2H), 0.88 (s, 18H); ¹³C NMR (101 MHz, CDCl₃): δ 171.2, 170.9, 170.4, 150.3, 148.5, 138.3, 131.6, 130.9, 129.5, 128.1, 71.2, 70.61, 70.59, 70.5, 70.4, 70.3, 58.6, 57.0, 43.2, 36.5, 35.6, 26.4, 16.1. HRMS (ESI) m/z: [M + H]⁺ calculated for: C₅₈H₈₂N₈O₁₄S₂: 1178.54; observed: 1179.6015.
N¹,N²⁰-bis((S)-1-((2S,4S)-4-hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)-3,6,9,12,15,18-hexaoxaicosanediamide (CMP98)

Following general method B, from compound 3 (7.12 mg, 0.028 mmol, 1 eq.), compound 8 (18.06, 0.040 mmol, 2.1 eq.), HATU (15.2 mg, 0.040 mmol, 2 eq.), HOAT (5.44 mg, 0.040 mmol, 2 eq.), DIPEA (7.45 mg, 0.0010 ml, 3 eq.), compound CMP98 was obtained as a white solid. Yield: 10.58 mg, 0.0089 mmol (45%). ¹H NMR (400 MHz, CDCl₃): δ 9.09 (s, 2H), 8.02 (s, 2H), 7.31 (d, J = 8.5 Hz, 4H), 7.22 (d, J = 8.0 Hz, 4H), 7.16 (d, J = 9.2 Hz, 2H), 4.75–4.64 (m, 4H), 4.51 (d, J = 8.9 Hz, 2H,), 4.41–4.37 (m, 2H), 4.24–4.17 (m, 2H), 3.94 (d, J = 3.2 Hz, 4H), 3.84–3.81 (m, 4H), 3.62–3.54 (m, 20H), 2.49–2.47 (m, 2H), 2.44 (s, 6H), 2.26–2.17 (m, 4H), 0.93 (s, 18H); ¹³C NMR (101 MHz, CDCl₃): δ 173.2, 171.5, 169.7, 151.8, 138.8, 132.9, 129.5, 129.2, 128.3, 71.2, 71.1, 70.6, 70.48, 70.45, 70.4, 70.3, 59.9, 58.5, 56.5, 43.2, 35.6, 35.2, 26.4, 15.0. HRMS (ESI)m/z: [M + H]⁺ calculated for: C₅₈H₈₂N₈O₁₄S₂: 1178.54; observed: 1179.6087.
1‐phenyl‐2,5,8,11,14-pentaoxahexadecan-16-ol (9)

Pentaethylene glycol (9.53 g, 50 mmol, 5 eq.) was added dropwise to a suspension of NaH 60% in mineral oil (800 mg, 20 mmol, 2.5 eq.) in 20 ml of DMF at 0 °C. The resulting mixture was stirred at r.t for 1 h. The reaction mixture was cooled to 0^oC, benzyl chloride (1 ml, 1.1 g, 8.72 mmol, 1 eq.) was added. The resulting mixture was stirred O/N at r.t. The reaction was quenched with a saturated solution of NH₄Cl and the aqueous phase was extracted with ethyl acetate (×3). The combined organic phases were dried over MgSO₄ and evaporated to dryness. The resulting oil was purified by column chromatography (from 0 to 60% of ethyl acetate in heptane) to afford the title compound as a oil. Yield: 2.055 g, 6.25 mmol (71%). ¹H NMR (400 MHz, CDCl₃): δ 7.28–7.19 (m, 5H), 4.50 (s, 2H), 3.66–3.52 (m, 20H), 2.50 (s, 1H). ¹³C NMR (101 MHz, CDCl₃): δ 138.2, 128.3, 127.8, 127.6, 73.2, 72.7, 70.61, 70.58, 70.53, 70.51, 70.2, 69.4, 61.7
tert-butyl 1-phenyl-2,5,8,11,14,17-hexaoxanonadecan-19-oate (10)

To a stirred solution of 9 (2.055 g, 6.25 mmol, 1 eq.) in 12.8 ml of DCM was added 37% solution of NaOH (12.8 ml), followed by tert-butylbromo acetate (4.882 g, 25 mmol, 4 eq.) and TBABr (2118 mg, 6.37 mmol, 1.02 eq.). The resulting solution was stired O/N at r.t. The reaction mixture was extracted with ethyl acetate (×3). The organic phases were combined and washed with brine (×1), dried over MgSO₄ and concentrate in vacuo. The resulting brow oil was purified by column chromatography (from 0 to 30% of ethyl acetate in petroleum) to afford the titled compound as colorless oil. Yield: 2.216 g, 5 mmol (80%). ¹H NMR (500 MHz, CDCl₃): δ 7.28–7.20 (m, 5H), 4.50 (s, 2H), 3.95 (s, 2H), 3.65–3.55 (m, 20H), 1.40 (s, 9H). ¹³C NMR (126 MHz, CDCl₃): δ169.7, 128.4, 127.7, 127.6, 81.5, 73.2, 70.7, 70.7, 70.6, 70.6, 69.4, 69.1, 28.1. MS (ESI)m/z: [(M-tBu) + H]⁺ calculated for: C₂₃H₃₈O₈: 442.26; observed: 387.20.
19,19-dimethyl-17-oxo-3,6,9,12,15,18-hexaoxaicosanoic acid (11)

10 (2.216 g, 5 mmol, 1 eq.) was dissolved in 75 ml of ethanol, Pd/C (10 wt%) was added and the resulting mixture was place under hydrogen and stirred at r.t. until complete conversion of the starting material. The reaction mixture was filtered through celite, the celite pad was washed few times using ethanol. The filtrate was concentrated in vacuum to give an oil that was used for the next step without further purification. Yield: 1764 g, 5 mmol (quantitative). BAIB (3.546 g, 11.01 mmol, 2.2 eq.) and TEMPO (171.87 mg, 1.10 mmol, 0.22 eq.) were added to a solution of ACN/H₂O 1:1 containing previous obtained oil (1.764 g, 5 mmol, 1 eq.). The resulting mixture was stirred at r.t until complete conversion of the starting material. The crude was purified using ISOLUTE® PE-AX anion exchange column. The column was equilibrate with methanol, the reaction mixture poured in the column and let it adsorbed in the pad. The column was washed with methanol (×3) to elute all the unbound material. Then, the titled product was eluted using a 50% solution of formic acid in methanol. The organic phase was evaporated to dryness to afford the title compound as oil. Yield: 1.200 g, 3.27 mmol (65%). ¹H NMR (400 MHz, CDCl₃): δ 4.12 (s, 2H), 3.98 (s, 2H), 3.72–3.60 (m, 16H), 1.43 (s, 9H). ¹³C NMR (101 MHz, CDCl₃): δ 172.6, 169.7, 81.6, 71.0, 70.59, 70.56, 70.54, 70.46, 70.38, 70.35, 70.30, 68.9, 68.8, 28.1.
tert-butyl (S)-19-((2S,4R)-4-hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidine-1-carbonyl)-20,20-dimethyl-17-oxo-3,6,9,12,15-pentaoxa-18-azahenicosanoate (12)

To a solution of PEG linker 11 (78.8 mg, 0.215 mmol, 1 eq.) in 1.5 ml DMF was added HATU (81.74 mg, 0.215 mmol, 1 eq.), HOAT (29.26 mg, 0.215 mmol, 1 eq.), DIPEA (80.13 mg, 0.106 ml, 0.645 mmol, 3 eq.) and the solution was stirred at room temperature for 5 min. Compound 7 (100 mg, 0.215 mmol, 1 eq.) was added and the pH of the reaction mixture was adjusted to > 9 by addition of DIPEA(80.13 mg, 0.106 ml, 0.645 mmol, 3 eq.). The mixture was stirred at room temperature until no presence of the starting materials was detected by LC-MS. The solvent was evaporated under reduced pressure to give the corresponding crude, which was purified by HPLC using a gradient of 20–95% v/v acetonitrile in 0.1% aqueous solution of ammonia to yield the titled compound as white solid. Yield: 75.6 mg, 0.094 mmol (44%). ¹H NMR (400 MHz, CDCl₃): δ 9.00 (s, 1H), 7.45 (t, J = 5.9 Hz, 1H), 7.39–7.33 (m, 4H), 7.29 (d, J = 8.9 Hz, 1H), 4.71 (t, J = 8.0 Hz, 1H), 4.59–4.48 (m, 3H), 4.34 (dd, J = 5.2, 14.6 Hz, 1H), 4.08–3.92 (m, 5H), 3.69–3.61 (m, 18H), 2.52 (s, 3H), 2.47–2.41 (m, 1H), 2.19–2.11 (m, 1H), 1.46 (s, 9H), 0.97 (s, 9H). ¹³C NMR (101 MHz, CDCl₃): δ 171.3, 171.1, 170.5, 170.0, 151.7, 139.1, 129.4, 128.3, 82.0, 71.1, 70.6, 70.4, 70.4, 70.3, 70.3, 70.2, 70.2, 68.9, 58.7, 57.3, 56.8, 43.1, 36.3, 35.1, 28.1, 26.4, 15.1. MS (ESI)m/z: [M + H]⁺ calculated for: C₃₈H₅₈N₄O₁₁S₂: 778.38; observed: 779.4.
N¹-((R)-1-((2R,4R)-4-hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)-N¹⁷-((S)-1-((2S,4R)-4-hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)-3,6,9,12,15-pentaoxaheptadecanediamide (CMP99)

Following general method B, from compound 12 (75.6 mg, 0.094 mmol, 1 eq.) and trifluoroacetic acid (1 ml in 1 ml of DCM), the carboxylic acid derivative was obtained as oil. The crude was used for the next step without further purification. Yield: 70 mg, 0.094 mmol (quantitative). MS (ESI) m/z: [M + H]⁺ calculated for: C₃₄H₅₀N₄O₁₁S: 722.32; observed: 723.3. Following general method B, from compound 13 (5.5 mg, 0.006 mmol, 1 eq.), compound 8 (2.77 mg, 0.006 mmol, 1 eq.), HATU (2.28 mg, 0.0.006 mmol, 1 eq.), HOAT (1 mg, 0.0.006 mmol, 1 eq.), DIPEA (2.23 mg, 0.002 ml, 0.018 mmol, 3 eq.), CMP99 was obtained as a white solid. Yield: 4.5 mg, 0.004 mmol (66%). ¹H NMR (400 MHz, CDCl3): δ 8.74 (s, 1H), 8.73 (s, 1H), 7.37–7.34 (m, 9H), 7.18 (d, J = 8.9 Hz, 1H), 4.76–4.64 (m, 3H), 4.59–4.44 (m, 5H), 4.37–4.26 (m, 2H), 4.05–3.59 (m, 27H), 2.52 (s, 6H), 2.31–2.11 (m, 4H), 0.96 (s, 9H), 0.95 (s, 9H). ¹³C NMR (101 MHz, CDCl₃): δ 173.0, 171.3, 170.0, 150.7, 145.4, 138.4, 129.53, 129.49, 128.2, 128.16, 71.2, 71.0, 70.54, 70.48, 70.4, 70.3, 58.4, 57.0, 56.7, 43.4, 35.2, 35.0, 26.4, 26.35, 15.9. HRMS (ESI)m/z: [M + H]⁺ calculated for: C₅₆H₇₈N₈O₁₃S₂: 1134.51; observed: 1135.5814.

Maniaci C., Hughes S.J., Testa A., Chen W., Lamont D.J., Rocha S., Alessi D.R., Romeo R, & Ciulli A. (2017). Homo-PROTACs: bivalent small-molecule dimerizers of the VHL E3 ubiquitin ligase to induce self-degradation. Nature Communications, 8, 830.

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Publication 2017

Amine-Terminated Triazine Dendrimer Synthesis

A solution of the generation two amine-terminated triazine dendrimer was prepared by dissolving 50.0 mg (0.0169 mmol) of the solids into 2.0 mL of the appropriate solvent (methanol or tetrahydrofuran). To this, methyl bromoacetate (37.2 mg, 22.4 µL, 0.244 mmol) corresponding to 1.2 mole equivalents per NH₂, was added. The reaction mixture was allowed to stir at room temperature for 2 hours. Formation of white precipitate was observed (presumably the hydrobromide salt of the partially substituted dendrimer). Then, 68.7 µL of a separately-prepared methanolic solution of potassium hydroxide (prepared by dissolving 206 mg of solid potassium hydroxide in 1.0 methanol under rigorous stirring) was added to the dendrimer-containing reaction mixture. The mixture was stirred at room temperature and sample was taken for analysis by MALDI-TOF-MS after 14 hours of reaction time. Further additions of 1.2 mole equivalents of methyl bromoacetate per NH₂ were required, each one accompanied by the addition of 68.7 µL of the methanolic potassium hydroxide solution. Progress of the reaction was monitored using MALDI-TOF-MS. A total of 8.4 mole equivalents of methyl bromoacetate per NH₂ had been added when signals corresponding to 25- and 26-ester-bearing dendrimers were observed along with the desired 24-ester-bearing species, along with signals corresponding to incompletely substituted dendrimers.
An aliquot of the reaction mixture corresponding to 10.0 mg of dendrimer was taken, and the solvent was removed under reduced pressure. The glassy material that remained was dissolved in 400 µL of 4M HCl and allowed to react at room temperature. Progress of the hydrolysis reaction was monitored using MALDI-TOF-MS. A 200 µL aliquot of the solution was then transferred into a preconditioned Centricon centrifugal filter device (Amicon Bioseparations) having a regenerated cellulose membrane with a 3,000 molecular weight cut-off. The retained solution was collected and used as is for further analysis.

Lalwani S., Chouai A., Perez L.M., Santiago V., Shaunak S, & Simanek E.E. (2009). Mimicking PAMAM Dendrimers with Ampholytic, Hybrid Triazine Dendrimers: A Comparison of Dispersity and Stability. Macromolecules, 42(17), 6723-3732.

Publication 2009

bromoacetate Dendrimers Esters Hydrolysis Medical Devices Methanol Moles Muscle Rigidity potassium hydroxide Pressure regenerated cellulose Sodium Chloride sodium polymetaphosphate Solvents Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization tetrahydrofuran Tissue, Membrane Triazines

Synthesis of N-Benzyloxycarbonyl-3,4-Methylenedioxyamphetamine

A solution of 5 g (12.7 mmol) of 1, 1.6 mL of ethyl bromoacetate, 170 mg of NaI, and 150 mL of acetonitrile was stirred at 80°C for 6 hrs, and then cooled down to room temperature. The reaction mixture was filtered, the filtrate was evaporated in vacuum, and the residue was purified on silica gel column (CH₂Cl₂/MeOH, 10/1) to give 2.82 g (49%) of the title compound. ESI(+)/MS(m/e): 422 [M-Br]^{+. 1}H NMR (DMSO-d₆, 300 MHz) δ/ppm = 10.021 (s, 1 H), 8.254 (d, J = 9.6 Hz, 1 H), 8.015 (d, J= 9.6 Hz, 1 H), 7.187 (s, 1 H), 7.097 (s, 1 H), 6.696 (s, 2 H), 4.436 (s, 2 H), 4.238 (dd, J₁ = 7.2 Hz, J₂ = 13.8 Hz, 2 H), 4.116 (s, 3 H), 4.093 (s, 3 H), 3.120 (t, J = 7.2 Hz, 2 H), 1.266 (t, J = 13.8 Hz, 3 H).27 (link)

Li G., Ren Y., Zhang X., Zhao S., Wang Y., Wu J., Peng S, & Zhao M. (2019). 13-[CH2CO-Cys-(Bzl)-OBzl]-Berberine: Exploring The Correlation Of Anti-Tumor Efficacy With ROS And Apoptosis Protein. OncoTargets and therapy, 12, 10651-10662.

Publication 2019

1H NMR acetonitrile ethyl bromoacetate Silica Gel Suby's G solution Sulfoxide, Dimethyl Vacuum

Selective Mono-N-tert-Butyl Acetylation of Cyclen

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Publication 2010

1H NMR Anus bromoacetate Carbon-13 Magnetic Resonance Spectroscopy Chloroform cyclen dimethylacetamide Ethyl Ether Filtration potassium bicarbonate Silica Gel Sodium Acetate Sulfate, Magnesium

Most recents protocols related to «Bromoacetate»

Synthesis of Carvone-Chitosan Derivatives

L-Carvone, chitosan (medium viscous, 200~400 mPa·s), and aryl aldehydes were purchased from Energy Chemical (Shanghai, China). 4-Methyl-thiosemicarbazide was provided by TCI (Tokyo, Japan). Ethyl bromoacetate, 5-amino-1,3,4-thiadiazole-2-thiol, chloroacetyl chloride, and other reagents/solvents were obtained from Macklin (Shanghai, China).

Li B., Duan W., Lin G., Ma X., Wen R, & Zhang Z. (2024). An Effective and Promising Strategy for Plant Protection: Synthesis of L-Carvone-Based Thiazolinone–Hydrazone/Nanochitosan Complexes with Antifungal Activity and Sustained Releasing Performance. International Journal of Molecular Sciences, 25(9), 4595.

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Publication 2024

Synthesis of L-Carvone-based Intermediate 3

A mixture of L-carvone 4-methyl-thiosemicarbazone 2 (16.8 g, 70.8 mmol) and sodium ethoxide (4.87 g, 71.6 mmol) in anhydrous ethanol (150 mL) was stirred at room temperature, and then ethyl bromoacetate (11.9 g, 71.3 mmol) was poured into the solution under continuous stirring. The reaction mixture was heated to reflux and kept for 4 h. After that, the reaction mixture was cooled down to room temperature, and the resulting precipitate was filtered out to obtain L-carvone-based intermediate 3 as a white solid with a yield of 93.0%.

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Publication 2024

Efficient Synthesis of N-Substituted Amines

To a solution of K₂CO₃ (10 mmol) and secondary amines 1a or 1b (5 mmol) in DMF (20 mL) was added ethyl bromoacetate (7.5 mmol). The reaction mixture was stirred at room temperature for 16 h and the reaction progress was monitored by Thin-Layer Chromatography (TLC) utilizing n-hexane:ethyl acetate (1:2). After completion reaction, the reaction mixture was diluted with ethyl acetate (20 mL), washed twice with water (20 mL) to remove DMF, and washed with brine. The collected organic layers were extracted and dried over Na₂SO₄, filtered, and concentrated to afford the product as colorless oil in high yields (80–95%).

Nazarian A., Abedinifar F., Hamedifar H., Hashempur M.H., Mahdavi M., Sepehri N, & Iraji A. (2024). Anticholinesterase activities of novel isoindolin-1,3-dione-based acetohydrazide derivatives: design, synthesis, biological evaluation, molecular dynamic study. BMC Chemistry, 18(1), 64.

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Publication 2024

Synthesis of 4-Substituted Chromenes

A solution of 1 (1 mmol), ethyl bromoacetate (1 mmol) in dry acetone (10 mL) containing anhydrous potassium carbonate (1 mmol) was refluxed for 12 h (TLC, n-hexane/ethylacetate 3:1). The organic layer was extracted using ethyl acetate, dried over anhydrous sodium sulphate. The solvent was evaporated under vacuum and a white solid was obtained in an extremely pure state and used without further purification.
Off white ppt, m.p.85–92 °C; yield: 90%; 1H NMR (500 MHz, DMSO-d6) δ 10.28 (s, 1H, CHO), 7.00 (s, 1H, CH pyranone ring), 6.07 (s, 1H, CH benzene ring ), 5.01 (s, 2H, OCH₂), 4.15 (dd, J = 12.2, 7.2 Hz, 2H, COOCH₂), 3.80 (s, 3H, OCH₃), 2.27 (s, 3H, CH₃), 1.20 (t, 3H, CH₃).

Abo-Salem H.M., El Souda S.S., Shafey H.I., Zoheir K.M., Ahmed K.M., Mahmoud K., Mahrous K.F, & Fawzy N.M. (2024). Synthesis, bioactivity assessment, molecular docking and ADMET studies of new chromone congeners exhibiting potent anticancer activity. Scientific Reports, 14, 9636.

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Publication 2024

Betaine Anhydrous Quantification by HPLC-MS

Betaine anhydrous (N, N, N-trimethylglycine) was acquired from Sigma-Aldrich (St. Louis, MO, USA) and diluted in 0.9% normal saline for IV infusion. Urethane was purchased from Sigma-Aldrich (Poznań, Poland).
For high-performance liquid chromatography-mass spectrometry (HPLC-MS) betaine hydrochloride, tert-butyl bromoacetate (TBBA), ammonia solution and ammonium formate were purchased from Sigma-Aldrich (St. Louis, MO, USA). Betaine-D3 hydrochloride was obtained from Toronto Chemicals Research (North York, Canada). The stock solution of betaine was prepared fresh in methanol. LC-MS grade acetonitrile, HPLC grade acetone, HPLC grade methanol and formic acid were obtained from J.T. Baker (Phillipsburg, New Jersey, USA). Ultra-pure water (Mili-Q water) was produced by a water purification system (Mili-Q, Millipore, Milford, MA, USA).

Mogilnicka I., Jaworska K., Koper M., Maksymiuk K., Szudzik M., Radkiewicz M., Chabowski D, & Ufnal M. (2024). Hypertensive rats show increased renal excretion and decreased tissue concentrations of glycine betaine, a protective osmolyte with diuretic properties. PLOS ONE, 19(1), e0294926.

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Publication 2024

Top products related to «Bromoacetate»

Ethyl bromoacetate by Merck Group

Sourced in Poland

Ethyl bromoacetate is a chemical compound commonly used in laboratory settings. It is a colorless liquid with a pungent odor. The core function of ethyl bromoacetate is as a versatile synthetic intermediate in organic chemistry.

Tert butyl bromoacetate by Merck Group

Sourced in Germany, Japan

Tert-butyl bromoacetate is a chemical compound used as a laboratory reagent. It is a colorless liquid with a pungent odor. The compound serves as a versatile synthon in organic synthesis.

Ethanol by Merck Group

Sourced in Germany, United States, United Kingdom, Italy, India, France, China, Australia, Spain, Canada, Switzerland, Japan, Brazil, Poland, Sao Tome and Principe, Singapore, Chile, Malaysia, Belgium, Macao, Mexico, Ireland, Sweden, Indonesia, Pakistan, Romania, Czechia, Denmark, Hungary, Egypt, Israel, Portugal, Taiwan, Province of China, Austria, Thailand

Ethanol is a clear, colorless liquid chemical compound commonly used in laboratory settings. It is a key component in various scientific applications, serving as a solvent, disinfectant, and fuel source. Ethanol has a molecular formula of C2H6O and a range of industrial and research uses.

Trifluoroacetic acid by Merck Group

Sourced in United States, Germany, United Kingdom, France, Spain, Italy, Australia, China, India, Sao Tome and Principe, Poland, Canada, Switzerland, Macao, Belgium, Netherlands, Czechia, Japan, Austria, Brazil, Denmark, Ireland

Trifluoroacetic acid is a colorless, corrosive liquid commonly used as a reagent in organic synthesis and analytical chemistry. It has the chemical formula CF3COOH.

Triethylamine by Merck Group

Sourced in United States, Germany, United Kingdom, France, Italy, India, Spain, Switzerland, Poland, Canada, China, Sao Tome and Principe, Australia, Belgium, Singapore, Sweden, Netherlands, Czechia

Triethylamine is a clear, colorless liquid used as a laboratory reagent. It is a tertiary amine with the chemical formula (CH3CH2)3N. Triethylamine serves as a base and is commonly employed in organic synthesis reactions.

Trifluoroacetic acid by Thermo Fisher Scientific

Sourced in United States, United Kingdom, Belgium, Germany, France

Trifluoroacetic acid is a commonly used reagent in organic chemistry. It is a colorless, fuming liquid with a pungent odor. The primary function of trifluoroacetic acid is as a strong acid and deprotecting agent in various chemical reactions and processes.

Acetonitrile by Merck Group

Sourced in Germany, United States, Italy, India, China, United Kingdom, France, Poland, Spain, Switzerland, Australia, Canada, Brazil, Sao Tome and Principe, Ireland, Belgium, Macao, Japan, Singapore, Mexico, Austria, Czechia, Bulgaria, Hungary, Egypt, Denmark, Chile, Malaysia, Israel, Croatia, Portugal, New Zealand, Romania, Norway, Sweden, Indonesia

Acetonitrile is a colorless, volatile, flammable liquid. It is a commonly used solvent in various analytical and chemical applications, including liquid chromatography, gas chromatography, and other laboratory procedures. Acetonitrile is known for its high polarity and ability to dissolve a wide range of organic compounds.

Di tert butyl dicarbonate by Merck Group

Sourced in Germany, United Kingdom

Di-tert-butyl dicarbonate is a common laboratory reagent used as a protecting group in organic synthesis. It is a colorless crystalline solid that is widely used in the protection of amine groups in the synthesis of various pharmaceutical and other chemical compounds.

Iron 3 chloride hexahydrate by Merck Group

Sourced in United States, Germany, Spain, Italy, India, Australia, United Kingdom, Ireland, Sao Tome and Principe, Czechia, Poland

Iron(III) chloride hexahydrate is a chemical compound with the formula FeCl3·6H2O. It is a crystalline solid that is soluble in water and other polar solvents. The compound is commonly used in various laboratory applications, serving as a source of iron(III) ions and as a flocculating agent.

Ammonium formate by Merck Group

Sourced in United States, Germany, United Kingdom, Italy, France, China, India, Switzerland, Spain, Canada, Poland, Sao Tome and Principe, Belgium, Czechia, Netherlands, Macao, Austria, Sweden, Japan, Hungary, Australia, Ireland

Ammonium formate is a chemical compound that is commonly used in various laboratory applications. It is a crystalline solid that is soluble in water and other polar solvents. Ammonium formate serves as a buffer in analytical techniques and is also used as a mobile phase additive in liquid chromatography.

What are the common uses of Bromoacetate in scientific research?

Bromoacetate is a versatile reagent used in a variety of chemical reactions, including nucleophilic substitution, alkylation, and ester formation. It is particularly useful in the synthesis of organic compounds and the modification of biomolecules. Researchers rely on optimized protocols and high-quality Bromoacetate products to ensure reproducible and efficient experiments.

How can researchers ensure they are using the most effective Bromoacetate protocols?

PubCompare.ai allows researchers to screen protocol literature more efficiently and leverage AI to pinpoint critical insights. The platform's AI-driven analysis can help identify the most effective Bromoacetate protocols related to your specific research goals, highlighting key differences in protocol effectiveness. This enables you to choose the best option for reproducibility and accuracy in your experiments.

Are there different variations or types of Bromoacetate that researchers should be aware of?

What are some common challenges researchers face when using Bromoacetate?

One of the main challenges with Bromoacetate is ensuring reproducibility and consistency in your experiments. Factors such as purity, stability, and handling can greatly impact the effectiveness of Bromoacetate. Researchers need to follow optimized protocols and use high-quality, well-characterized Bromoacetate products to overcome these challenges and achieve reliable results.

How can PubCompare.ai help researchers find the most reliable and efficient Bromoacetate protocols?

PubCompare.ai's AI-driven comparisons of literature, preprints, and patents can help researchers identify the most reliable and effiecient methods for their Bromoacetate research needs. The platform's analysis can pinpoit key differences in protocol effectiveness, enabling researchers to choose the best option for reproducibility and accuracy. This helps overcome common challenges and ensures optimal use of Bromoacetate in your experiments.

More about "Bromoacetate"

Bromoacetate, also known as 2-Bromoethanoate or Ethyl 2-Bromoacetate, is a versatile chemical compound with the formula CH2BrCOO-.
It is widely used in scientific research and organic synthesis due to its reactivity and versatility.
Bromoacetate is commonly employed in various chemical reactions, including nucleophilic substitution, alkylation, and ester formation.
It is particularly useful in the synthesis of organic compounds, as well as the modification of biomolecules.
Researchers often utilize optimized protocols and high-quality Bromoacetate products to ensure reproducible and efficient experiments.
Related compounds, such as Ethyl bromoacetate and Tert-butyl bromoacetate, are also employed in similar applications.
These compounds can be used in conjunction with other reagents, such as Ethanol, Trifluoroacetic acid, Triethylamine, Acetonitrile, Di-tert-butyl dicarbonate, and Iron(III) chloride hexahydrate, to facilitate various chemical transformations.
PubCompare.ai's AI-driven comparisons of literature, preprints, and patents can help researchers identify the most reliable and efficient methods for their Bromoacetate-based experiments.
This can include the identification of optimized protocols, the comparison of product quality, and the evaluation of experimental outcomes, ultimately supporting reproducible and efficient Bromoacetae research.
By leveraging the insights and tools provided by PubCompare.ai, researchers can ensure that their Bromoacetate experiments are conducted using the best available protocols and products, leading to more reliable and reproducible results.
This, in turn, can contribute to the advancement of scientific knowledge and the development of innovative applications in fields such as organic chemistry, biochemistry, and materials science.