Chiral resolution of an intermediate in diltiazem synthesis using lipase PS immobilized with sucrose

An enzymatic method for the preparation of (2S,3S)-threo-alkyl-2-hydroxy-3-(4-methoxyphenyl)-3-(2-X-phenylthio)propionate, where X=NO2, NH2, NHCOCH3, NHCOCF3, NHCO2CH3, NHCO2C(CH3)3 or NHCHO and R is an alkyl group, e.g., CH3, or CH2CH3 in an essentially anhydrous organic solvent is described. In th...

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Bibliographic Details
Main Authors HYTOENEN; MARTTI, SUNDHOLM; OSKARI, KANERVA; LIISA, KAIRISALO; PEKKA
Format Patent
LanguageEnglish
Published 07.05.1996
Edition6
Subjects
BEER
BIOCHEMISTRY
CHEMISTRY
ENZYMOLOGY
FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIREDCHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERSFROM A RACEMIC MIXTURE
METALLURGY
MICROBIOLOGY
MUTATION OR GENETIC ENGINEERING
PROCESSES USING MICROORGANISMS
SPIRITS
VINEGAR
WINE
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Summary:An enzymatic method for the preparation of (2S,3S)-threo-alkyl-2-hydroxy-3-(4-methoxyphenyl)-3-(2-X-phenylthio)propionate, where X=NO2, NH2, NHCOCH3, NHCOCF3, NHCO2CH3, NHCO2C(CH3)3 or NHCHO and R is an alkyl group, e.g., CH3, or CH2CH3 in an essentially anhydrous organic solvent is described. In this method a lipase which stereospecifically acylates the (2R,3R)-enantiomer of the racemic mixture is used. After enzymatic reaction, the (2S,3S)-enantiomer and the acylated (2R,3R)-compound are separated, e.g., by flash-chromatography or by fraction crystallization of the (2S,3S)-compound from the reaction mixture.
Bibliography:Application Number: US19940215529