Optical resolution of alkyl 1,4-benzodioxan-2-carboxylates using

Details Optical resolution of alkyl 1,4-benzodioxan-2-carboxylates using Optical resolution of alkyl 1,4-benzodioxan-2-carboxylates using

1995-06-07

1996-06-25

Wityshyn, Michael G.

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, C12P 4100

Patent

active

055299296

ABSTRACT:
A process for resolving racemic alkyl 1,4-benzodioxan-2-carboxylates useful as intermediates in the synthesis of optically pure pharmaceutical compounds such as (S)-doxazosin is disclosed. The process utilizes a microbial enzyme derived from Serratia marcescens to catalyze the enantioselective hydrolysis of the alkyl (S)-1,4-benzodioxan-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 for subsequent pharmaceutical synthesis. The nonhydrolyzed alkyl (R)-1,4-benzodioxan-2-carboxylate enantiomer can also be isolated and racemized, and the enzymatic hydrolysis reaction repeated.

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