Chiralpakad column

Manufactured by Daicel

The ChiralPakAD column is a high-performance liquid chromatography (HPLC) column used for the separation and analysis of chiral compounds. It utilizes a cellulose-based stationary phase to provide efficient enantioseparation of a wide range of racemic mixtures.

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Lab products found in correlation

Hplc system, by Daicel (2 mentions)

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ChiralpakAD-H chiral column

5 protocols using chiralpakad column

Enantioselective Synthesis of M-Tirofiban

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To a solution of compound 4 (150 mg, 299 μmol, 1.00 eq, HCl) in DCM (3 mL) was added Boc2O (78.3 mg, 359 μmol, 82.4 uL, 1.20 eq) and Et3N (45.3 mg, 448 μmol, 62.4 uL, 1.50 eq) at 0°C. The resulting mixture was stirred at 20 °C for 4 hrs. LCMS showed no compound 4 remained, and one major new peak (Rt = 0.873, m/z = 466) with desired product was detected. The reaction mixture was poured into 20% citric acid (~ 5 mL) and extracted with EtOAc (~ 20 mL, 10 mL), the organic layers were washed with brine (10 mL), dried over Na₂SO₄ and concentrated to give the product. The product was separated further by chiral SFC (Thar SFC 80) using a DAICEL Chiralpak AD column (250mm×30mm, 10um); mobile phase: A: CO₂ and isocratic elution with B: 38% 0.1%NH3H2O ETOH for 6 min at 40°C with a system back pressure of 100 bar. The fractions after SFC were concentrated to give compound 5A (65.0 mg, 115 μmol, 76.9% yield) as a light-yellow solid and Compound 5B (70.0 mg, 123. μmol, 82.8% yield) as a light-yellow solid. Comparison of the elution in SFC of the 95% pure, chiral M-tirofiban synthesized in scheme 1 showed that peak 2 in SFC was compound 5A, the desired (S)-M-tirofiban; peak 1 was compound 5B, the undesired (R)-M-tirofiban isomer.

Lin F.Y., Li J., Xie Y., Zhu J., Nguyen T.T., Zhang Y., Zhu J, & Springer T.A. (2022). A general chemical principle for creating closure-stabilizing integrin inhibitors. Cell, 185(19), 3533-3550.e27.

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Chiral Separation of Pyrido[4,3-b]indol Derivative

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The
title compound was obtained after semipreparative chiral separation
of racemic (6-fluoro-1,9-dimethyl-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl)-(5-(trifluoromethyl)-1H-pyrazol-3-yl)methanone (32) on a Daicel ChiralPak
AD column (250 × 10 mm ID, particle size 10 μm) using heptane/2-propanol
(95:5) as the mobile phase, as a white solid (0.003 g, 11%). NMR spectra,
UPLC-MS data, and HRMS data are consistent with the corresponding
racemate. Enantiomeric excess was determined to be 63% (least value
due to peak-tailing) after chiral HPLC analysis.

Brindani N., Gianotti A., Giovani S., Giacomina F., Di Fruscia P., Sorana F., Bertozzi S.M., Ottonello G., Goldoni L., Penna I., Russo D., Summa M., Bertorelli R., Ferrera L., Pesce E., Sondo E., Galietta L.J., Bandiera T., Pedemonte N, & Bertozzi F. (2020). Identification, Structure–Activity Relationship, and Biological Characterization of 2,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indoles as a Novel Class of CFTR Potentiators. Journal of Medicinal Chemistry, 63(19), 11169-11194.

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Separation of Enantiomers of Compound 435

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Example 8

[Figure (not displayed)]

Example 9

Separation of Enantiomers of Compound 435.

Compound 435 obtained from Example 8 above (0.32 g) was dissolved in a minimal amount of iPrOH (5 mL, HPLC grade, heating was required) and diluted with hexane (4 mL, HPLC grade). Enantiomer separation was achieved using a Waters HPLC system equipped with a preparative Daicel CHIRALPAK® AD column (20×250 mm). For the first minute of the run, the mobile phase was 80% hexane and 20% iPrOH along with 0.1% diethylamine. After the first minute a gradient to 75% hexane and 25% iPrOH along with 0.1% diethylamine over 15 minutes was used, followed by holding at this solvent ratio for 17 minutes at a flow rate of 18 mL/min. This method resulted in baseline separation with Compound 435(R) eluting first (21.9 min), followed by Compound 435(S) (25.2 min). Fractions containing each enantiomer were concentrated under reduced pressure to give 0.12 g each of 435(R) (mp 108.0-108.1° C.) and 435(S) (mp107.6-107.7° C.) as off-white solids.

US10335413B2. Substituted xanthine derivatives (2019-07-02). Concert Pharmaceuticals, Inc. [US]. Inventors: Roger D. Tung [US], Julie F. Liu [US], Scott L. Harbeson [US].

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Chiral Separation of Pyrido[4,3-b]indol Derivative

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The
title compound was obtained after semipreparative chiral separation
of racemic (6-fluoro-1,9-dimethyl-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl)-(5-(trifluoromethyl)-1H-pyrazol-3-yl)methanone (32) on a Daicel ChiralPak
AD column (250 × 10 mm ID, particle size 10 μm) using heptane/2-propanol
(95:5) as the mobile phase, as a white solid (0.005 g, 19%). NMR spectra,
UPLC-MS data, and HRMS data are consistent with the corresponding
racemate 32. Enantiomeric excess was determined to be
97% after chiral HPLC analysis. [α]₅₈₉²⁵ +57.7 (c 1.0, CH₃OH).

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Separation and Characterization of Compound 419 Enantiomers

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Example 6

[Figure (not displayed)]

Example 7

Separation of Enantiomers of Compound 419.

Compound 419 obtained from Example 6 above (0.38 g) was dissolved in a minimal amount of iPrOH (6 mL, HPLC grade, heating required) and diluted with hexane (4 mL, HPLC grade). Enantiomeric separation was achieved using a Waters HPLC system equipped with a preparative Daicel CHIRALPAK® AD column (20×250 mm). For the first minute of the run, the mobile phase was 80% hexane and 20% iPrOH along with 0.1% diethylamine. After the first minute a gradient to 75% hexane and 25% iPrOH along with 0.1% diethylamine over 15 minutes was used, followed by holding at this solvent ratio for 17 minutes at a flow rate of 18 mL/min. This method resulted in baseline separation with 419(R) eluting first (21.0 min), followed by 419(5) (24.1 min). Fractions containing each enantiomer were concentrated under reduced pressure to give 0.16 g each of 419(R) (mp 107.8-108.8° C.) and 419(5) (mp 108.3-108.4° C.) as off-white solids.

US10335413B2. Substituted xanthine derivatives (2019-07-02). Concert Pharmaceuticals, Inc. [US]. Inventors: Roger D. Tung [US], Julie F. Liu [US], Scott L. Harbeson [US].

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