Optical resolution of alkyl chroman-2-carboxylates

Details Optical resolution of alkyl chroman-2-carboxylates Optical resolution of alkyl chroman-2-carboxylates

1995-06-07

1997-08-19

Richter, Johann

Chemistry: molecular biology and microbiology

Process of utilizing an enzyme or micro-organism to destroy...

Resolution of optical isomers or purification of organic...

435125, 435881, 549405, C12P 4100

Patent

active

056587961

ABSTRACT:
Described herein is a process for resolving a racemic (C>3) alkyl (R, S) chroman-2-carboxylate compound useful as intermediates in the synthesis of optically pure pharmaceutical compounds is disclosed. The process utilizes a microbial enzyme derived from Serratia marcescens to catalyze the enantioselective hydrolysis of the (C>3) alkyl (S)-chroman-2-carboxylate enantiomer of the racemic mixture to its corresponding carboxylic acid at a faster rate than the R-enantiomer. An enantiomerically pure S-configured carboxylic acid is thereby formed which can undergo acidic esterification to provide an optically pure (C>3) alkyl (S)-chroman-2-carboxylate intermediate for subsequent pharmaceutical synthesis. The nonhydrolyzed (C>3) alkyl (R)-chroman-2-carboxylate enantiomer can also be isolated to provide an optically pure pharmaceutical precursor.

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"Quantitative Analyses of Biochemical Kinetic Resolutions of Enantiomers", Chen et al., J. Am. Chem. Soc. 104, 7294-7299 (1982).

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