All solvents for the synthesis were purified by passing commercially available pre-dried, oxygen-free formulations through activated alumina columns. Reactions were monitored by TLC or LC-MS and the products were purified by flash column chromatography unless otherwise mentioned. NMR spectra were recorded on a Bruker AN400 or AN600 instrument. The chemical shifts for 1H and 13C NMR spectra are reported in ppm (δ) relative to the 1H and 13C signals in the solvent (CDCl3: δ 7.26, 77.16 ppm; CD3CN: δ 1.94, 118.26 ppm; CD3OD: δ 3.31, 49.00 ppm) and the multiplicities are presented as follows: s = singlet, d = doublet, t = triplet, m = multiplet. LC-MS was performed on an Agilent 1260 HPLC machine coupled to a 6120 single quadrupole MS detector using an Agilent Eclipse XDB-C18 5 μm 4.6×150 mm column.
Eclipse xdb c18 5 μm
Manufactured by Agilent Technologies
The Eclipse XDB-C18 5 μm is a reversed-phase high-performance liquid chromatography (HPLC) column. It features a 5 μm particle size and a C18 stationary phase. The column is designed for the separation and analysis of a wide range of organic compounds.
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5 protocols using eclipse xdb c18 5 μm
1
Purification and Characterization of Organic Compounds
2
Purification and Characterization of Organic Compounds
3
Synthesis and Purification of Cbl-DFO
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Cbl-DFO was synthesized through
the activation of the 5′-ribose-hydroxyl group with CDT. CDT
(34 mg, 0.261 mmol, 7.2 equiv) was added with cyano-Cbl (50 mg, 0.0368
mmol, 1 equiv) in anhydrous DMSO (3 mL) at 40 °C for 2 h. DFO
(208 mg, 0.313 mmol, 7.4 equiv) was added to the reaction mixture
and mixed overnight. Purification of Cbl-DFO was done using reversed-phase
(RP)-HPLC (Agilent 1200) with a C18 column (Agilent Eclipse XDB-C18
5 μm, 4.6 mm × 150 mm) at a flow rate of 1 mL/min. Detection
was done using a UV–vis detector at 360 nm. RP-HPLC method:
(A) 0.1% trifluoroacetic acid water and (B) MeCN as solvents with
the following gradient: 1% B to 70% B over 15 min, (Rt = 9.4 min). Purity was ≥97% via RP-HPLC. Yield:
30–40%. 1H NMR analysis of the aromatic region:
7.178 (s, 1H), 7.016 (s, 1H), 6.426 (s, 1H), 6.218 (s, 1H), 5.989
(s, 1H). Liquid chromatography–mass spectrometry (LC–MS)
analysis: expected m/z: 1942; observed:
972 [M + 2H]2+ and 648 [M + 3H]3+.
the activation of the 5′-ribose-hydroxyl group with CDT. CDT
(34 mg, 0.261 mmol, 7.2 equiv) was added with cyano-Cbl (50 mg, 0.0368
mmol, 1 equiv) in anhydrous DMSO (3 mL) at 40 °C for 2 h. DFO
(208 mg, 0.313 mmol, 7.4 equiv) was added to the reaction mixture
and mixed overnight. Purification of Cbl-DFO was done using reversed-phase
(RP)-HPLC (Agilent 1200) with a C18 column (Agilent Eclipse XDB-C18
5 μm, 4.6 mm × 150 mm) at a flow rate of 1 mL/min. Detection
was done using a UV–vis detector at 360 nm. RP-HPLC method:
(A) 0.1% trifluoroacetic acid water and (B) MeCN as solvents with
the following gradient: 1% B to 70% B over 15 min, (Rt = 9.4 min). Purity was ≥97% via RP-HPLC. Yield:
30–40%. 1H NMR analysis of the aromatic region:
7.178 (s, 1H), 7.016 (s, 1H), 6.426 (s, 1H), 6.218 (s, 1H), 5.989
(s, 1H). Liquid chromatography–mass spectrometry (LC–MS)
analysis: expected m/z: 1942; observed:
972 [M + 2H]2+ and 648 [M + 3H]3+.
4
Purification and Characterization of Organic Compounds
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All solvents for the synthesis were purified by passing commercially available pre-dried, oxygen-free formulations through activated alumina columns. Reactions were monitored by TLC or LC-MS and the products were purified by flash column chromatography unless otherwise mentioned. NMR spectra were recorded on a Bruker AN400 or AN600 instrument. The chemical shifts for 1H and 13C NMR spectra are reported in ppm (δ) relative to the 1H and 13C signals in the solvent (CDCl3: δ 7.26, 77.16 ppm; CD3CN: δ 1.94, 118.26 ppm; CD3OD: δ 3.31, 49.00 ppm) and the multiplicities are presented as follows: s = singlet, d = doublet, t = triplet, m = multiplet. LC-MS was performed on an Agilent 1260 HPLC machine coupled to a 6120 single quadrupole MS detector using an Agilent Eclipse XDB-C18 5 μm 4.6×150 mm column.
5
Synthesis and Purification of Compound 6
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Compound 16 (0.30g, 0.63 mmol) was added to DCM (20 mL). While stirring, sulfuric acid (0.491 g, 5.00 mmol) was added. The solution was heated to 40°C overnight. The DCM was decanted and a minimum amount of ethyl acetate was added to the precipitated after which a slurry was formed by sonication. The crude product was suspended by pouring the slurry into a 50 mL Falcon tube with ice-cold ether (35 mL). The suspension was centrifuged and the supernatant was discarded. The pellet was air dried and purified by high pressure liquid chromatography The pellet was air dried and purified by high pressure liquid chromatography on a Shimadzu Prominence HPLC system over a 9.4 mm x 250 mm semi-preparative Agilent Eclipse XDB-C18 5 μm with UV detection at 280 nm. A gradient ran from 90% H2O (+0.1% TFA)/10% CH3CN (+0.1% TFA) to 75% H2O (+0.1% TFA)/25% CH3CN (+0.1% TFA) over 7 minutes, to 50% H2O (+0.1% TFA)/50% CH3CN (+0.1% TFA) over 13 minutes. The fractions were collected and lyophilized, yielding compound 6 as a light brown solid (0.107 g, 17%).
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