OPTICAL RESOLUTION OF ALKYL CHROMAN-2-CARBOXYLATES

摘要

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.