Small scale separation of isoxazole structurally related analogues by chiral supercritical fluid chromatography

Zehani, Yasmine; Lemaire, Lucas; Millet, Régis; Lipka, Emmanuelle

doi:10.1016/j.chroma.2017.05.028

Cited by 14 publications

(3 citation statements)

References 29 publications

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“…To provide an enantiomerically pure ibuprofen medication to maximize benefit and minimize risk to the patient, preparative purification methods are required. There are several methods to produce enantiomerically pure compounds including preparative highperformance liquid chromatography (HPLC), [11][12][13] supercritical fluid chromatography (SFC), [14][15][16] and diastereomeric crystallization. 17,18 Diastereomeric crystallization is a commonly applied technique, but it is often confined to a particular case, requiring reagents that are only effective for a particular system.…”

Section: Introductionmentioning

confidence: 99%

Rapid Purification of Drug Enantiomers using Supercritical Fluid Chromatographic Method: Ibuprofen as a Model Compound

Lee¹,

Gahm²,

Jin³

et al. 2021

IJPER

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Background:The purification of drug enantiomers is an essential technique because pharmacological activity differs depending on individual enantiomers. Nowadays, supercritical fluid technology is utilized for various purposes in the pharmaceutical field. Methodology: In this study, an efficient and streamlined method development strategy for finding an effective analytical method in supercritical fluid chromatography (SFC) is presented in detail for scaling up to preparative scale and achieving enantiomerically pure product, using ibuprofen as a model compound. Results: Through the optimized preparative method presented, the individual (R) enantiomer of the commercial racemate of ibuprofen can be obtained with a recovery yield of 80.0% and an enantiomeric excess of 95.1 and the individual (S) enantiomer can be obtained with a recovery yield of 77.6% with an enantiomeric excess of 99.3, respectively. Conclusion: The use of analytical and preparative SFC systems has advantages over the conventional chromatography systems in terms of separation time, reduced solvent consumption and high productivity for ibuprofen's enantiomeric purification.

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Section: Introductionmentioning

confidence: 99%

Rapid Purification of Drug Enantiomers using Supercritical Fluid Chromatographic Method: Ibuprofen as a Model Compound

Lee¹,

Gahm²,

Jin³

et al. 2021

IJPER

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show abstract

“…Now more than ever, analytical and preparative enantiomeric separations play a crucial role in industry and academic research [1]. There are a wide variety of methods to achieve and analyze enantiomerically pure compounds, including liquid chromatography (LC) [2,3], supercritical fluid chromatography [4,5,6], diastereomeric crystallization [7,8], membranes [9,10], asymmetric catalysis [11], simulated moving bed [12,13], dynamic and enzyme-mediated kinetic resolution [14,15], among others.…”

Section: Introductionmentioning

confidence: 99%

Chiral Stationary Phases for Liquid Chromatography: Recent Developments

et al. 2019

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The planning and development of new chiral stationary phases (CSPs) for liquid chromatography (LC) are considered as continuous and evolutionary issues since the introduction of the first CSP in 1938. The main objectives of the development strategies were to attempt the improvement of the chromatographic enantioresolution performance of the CSPs as well as enlarge their versatility and range of applications. Additionally, the transition to ultra-high-performance LC were underscored. The most recent strategies have comprised the introduction of new chiral selectors, the use of new materials as chromatographic supports or the reduction of its particle size, and the application of different synthetic approaches for preparation of CSPs. This review gathered the most recent developments associated to the different types of CSPs providing an overview of the relevant advances that are arising on LC.

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“…Therefore, the separation of racemates is required for applications in many different areas such as the pharmaceutical industry, environmental chemistry, food chemistry and agriculture. [1][2][3][4][5][6] In the chiral resolution of a racemic mixtures in chemistry, the various methods such as asymmetric synthesis, chromatographic separation, chemical or enzymatic kinetic resolution, and diastereomeric crystallization were utilized to acquire selectively the desired enantiomer. Among the methods used for the chiral resolution, enantio separation by HPLC using CSPs is currently the most popular one.…”

Section: Introductionmentioning

confidence: 99%

Design, preparation and application of a Pirkle-type chiral stationary phase for enantioseparation of some racemic organic acids and molecular dynamics studies

Çakmak¹,

Ercan²,

Sünkür³

et al. 2017

Org. Commun.

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This study consists of two parts. In the first part of the study; a Pirkle-type chiral stationary phase was prepared by synthesizing an aromatic amine derivative of (R)-2-amino-1-butanol as a chiral selector and binding to L-tyrosine-modified cyanogen bromide (CNBr)-activated Sepharose 4B and then, packed into the separation column. The chromatographic performance of the separation column was evaluated with racemic mandelic acid and 2-phenylpropionic acid by using phosphate buffers at three different pHs as mobile phase. In the resolution processes, the prepared solutions were loaded onto the separation column at two different concentrations and at three different pHs for each racemic organic acid, separately. Enantiomeric excess (ee%) of the eluates was determined on CHIRALPAK AD-H chiral analytical column by HPLC. The maximum ee% for mandelic acid and 2-phenylpropionic acid was determined to be 60.84 and 27.4, respectively. Separation factors (k 1 ' , k 2 ' , α, and Rs) were calculated for each acid. The structures of the obtained compounds were characterized using the spectroscopic methods (NMR, and elemental analysis). In the second part of the study; enantioselective interactions between the prepared CSP and the analytes have been widely studied by docking, molecular dynamics simulation and quantum mechanical computation methods. The reason of column eluation of rac-2-phenylpropionic acid with lower enantiomeric yield was explained by these techniques.

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Small scale separation of isoxazole structurally related analogues by chiral supercritical fluid chromatography

Cited by 14 publications

References 29 publications

Rapid Purification of Drug Enantiomers using Supercritical Fluid Chromatographic Method: Ibuprofen as a Model Compound

Rapid Purification of Drug Enantiomers using Supercritical Fluid Chromatographic Method: Ibuprofen as a Model Compound

Chiral Stationary Phases for Liquid Chromatography: Recent Developments

Design, preparation and application of a Pirkle-type chiral stationary phase for enantioseparation of some racemic organic acids and molecular dynamics studies

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