Drug synthesis methods and manufacturing technology preparative chromatographic separation of ibuprofen enantiomers on Whelk-O1 chiral stationary phase

Reshetova, E. N.; Горбунов, А. А.

doi:10.1007/s11094-012-0848-3

Cited by 2 publications

(3 citation statements)

References 15 publications

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“…Gowramma et al (2011) reported that the retention times were 6.3 and 10.4 min for (R) and (S) ibuprofen respectively on Lux 5μ cellulose column in a mobile phase of mixture of perchloric acid (pH 2) and acetonitrile with their optimized HPLC procedure. Another result (Reshetova, et al 2012) showed that although it may depend on parameters such as temperature, sample volume, mobilephase composition, on the chiral stationary phase (S,S)-Whelk-O1 in a prep-LC system, separation time of (R) and (S) ibuprofen took more than 15 min. Furthermore, the concentration and injection volume of the sample was minimized to complete separation.…”

Section: Preparative Sfcmentioning

confidence: 99%

“…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%

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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: Preparative Sfcmentioning

confidence: 99%

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

View full text Add to dashboard Cite

show abstract

“…[1] So the separation of racemic ibuprofen has a great realistic significance. For instance, Reshetova and coworkers [2] used chiral chromatography to separate ibuprofen enantiomers, with (S,S)-Whelk-O1 as the chiral stationary phase and hexane∶ethanol modified with acetic acid as the eluents. Finally, they got superior target enantiomers in both purity and yield.…”

Section: Introductionmentioning

confidence: 99%

Preparation of Thermosensitive Hollow Imprinted Microspheres via Combining Distillation Precipitation Polymerization and Thiol‐ene Click Chemistry

Guo

Wang

Shan³

2014

Chin. J. Chem.

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Hollow molecular imprinted polymer microspheres were prepared by distillation precipitation polymerization with (S)-(＋)-ibuprofen (S-IBF) as template molecule and acrylamide (AM) as functional monomer. Using the silicon dioxide (SiO 2 , 180 nm) modified by 3-(trimethoxysilyl)propyl methacrylate (MPS) as the template microspheres, the molecular imprinted shells were coated on successfully (SiO 2 @MIPs). The thermosensitive SiO 2 @MIPs-PNIPAM core-shell microspheres were subsequently prepared by grafting the PNIPAM chains (M n ＝ 1.21×10 4 g/mol, polydispersity index＝1.30), which were prepared by reversible addition-fragmentation chain transfer (RAFT) polymerization, on the surface of SiO 2 @MIPs microspheres via the thiol-ene click chemistry. The grafting density of PNIPAM brushes on the SiO 2 @MIPs microspheres was about 0.18 chains/nm 2 . After HF etching, the hollow imprinted microspheres were finally obtained. For thermosensitivity analysis, the phase transition temperatures of multifunctional nanoparticles were measured by DSL at 25 and 45 ℃ respectively, ℃ and the sizes of the microspheres changed by about 35 nm. The modified microspheres presented excellent controlled release property to S-IBF, moreover about half amount of the adsorptions passed into acetonitrile-water solution through the specific holes of imprinted shell at 25 ℃ under vibration.

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Drug synthesis methods and manufacturing technology preparative chromatographic separation of ibuprofen enantiomers on Whelk-O1 chiral stationary phase

Cited by 2 publications

References 15 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

Preparation of Thermosensitive Hollow Imprinted Microspheres via Combining Distillation Precipitation Polymerization and Thiol‐ene Click Chemistry

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