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

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

C - Chemistry, Metallurgy

12

P

C12P 41/00 (2006.01) C07D 319/20 (2006.01) C12P 17/06 (2006.01)

Patent

CA 2231456

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.

L'invention décrit un procédé permettant de séparer des alkyl 1,4-benzodioxan-2-carboxylates alkyliques racémiques utiles comme intermédiaires dans la synthèse de composés optiquement purs tels que la (S)-doxazosine. Ledit procédé consiste à utiliser une enzyme microbienne dérivée de Serratia marcescens pour catalyser l'hydrolyse énantiosélective de l'énantiomère (S)-1,4-benzodioxan-2-carboxylate alkylique du mélange racémique pour produire son acide carboxylique correspondant à une vitesse plus rapide que l'énantiomère R. Un acide carboxylique à configuration S, pur du point de vue énantiomérique, est ainsi obtenu pour synthèse pharmaceutique ultérieure. L'énantiomère (R)-1,4-benzodioxan-2-carboxylate alkylique non hydrolysé peut également être isolé et racémisé, et la réaction d'hydrolyse enzymatique répétée.

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