Method for preparing an r- or s-form of alpha-substituted...

Details Method for preparing an r- or s-form of alpha-substituted... Method for preparing an r- or s-form of alpha-substituted...

C - Chemistry, Metallurgy

12

P

C12P 7/40 (2006.01) C12P 41/00 (2006.01)

Patent

CA 2410441

Disclosed is a method for preparing an R- or S-forms of alpha-substituted heterocyclic carboxylic acid (alpha-HCCA) and a counter enantiomeric form of alpha-substituted heterocyclic carboxylic acid ester thereto by use of an enzyme. A racemic alpha-HCCA is reacted with alcohol to give a racemic alpha- HCCA ester, which is then brought into contact with an enzyme with enantioselectivity, whereby either R-form or S-form of the racemate is hydrolyzed. Extraction with an organic solvent can obtain enantiomers of the alpha-HCCA ester. Thus, a certain enantiomeric form of alpha-HCCA and a counter enantiomeric form of alpha-HCCA ester thereto, respectively can be prepared with high optical purity at high yields as well as at low cost.

L'invention concerne un procédé de fabrication de forme R ou S d'acide carboxylique hétérocyclique à substitution alpha (alpha HCCA), et de forme contre-énantiomère d'ester d'acide carboxylique hétérocyclique à substitution alpha correspondante, à base d'enzyme. On établit une réaction entre un alpha-HCCA racémique et de l'alcool pour donner un ester d'alpha-HCCA racémique, lequel est ensuite mis en contact avec une enzyme à énantiosélectivité, moyennant quoi la forme R ou S du racémate est hydrolysée. L'extraction avec un solvant organique donne des énantiomères de l'ester d'alpha-HCCA. On est donc en présence d'une certaine forme énantiomère d'alpha-HCCA, et de forme contre-énantiomère d'ester d'alpha-HCCA correspondante, respectivement, que l'on peut préparer en assurant une pureté optique et un rendement élevés, pour un coût peu important.

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