Enzymatic resolution process
AssigneeE. R. Squibb & Sons, Inc.
InventorsJeffrey M. Howell, Ramesh N. Patel, Laszlo J. Szarka
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Abstract
A novel enzymatic resolution process for preparing resolved compounds of the formula ##STR1## with improved yields and high optical purity is disclosed. Compounds of formula I' are useful, for example, as intermediates for the preparation of physiologically active compounds, e.g. captopril, zofenopril and endopeptidase inhibitor.
Claims1
A process for the preparation of a compound of the formula ##STR33## which comprises A) coupling Boc alanine with a proline benzyl ester hydrochloride salt to form a Boc protected alanine proline benzyl ester having the formula ##STR34## B) reacting the product of step A with trifluoroacetic acid and tosic acid to produce an alaproline benzyl ester tosic acid of formula ##STR35## C) preparing a resolved carboxylic acid of the formula ##STR36## by treating a compound of formula ##STR37## with an enzyme of microorganism containing an enzyme, capable of asymmetrically hydrolyzing the thioester bond in the presence of a solvent;
- D) alkylating the resolved carboxylic acid with the alaproline benzyl ester tosic acid of step B to form a compound of formula ##STR38## E) saponifying the above compound to provide the desired product.
Dependencies are inferred from the claim text.