Crystallization-Induced Asymmetric Transformation: Stereospecific Synthesis of a Potent Peripheral CCK Antagonist

Abstract

An efficient, catalytic method for the total conversion of a racemate into a single enantiomer is reported. The combined, in situ resolution-racemization was applied to 3(RS)-amino-l,3-dihydro-l-methyl-5-phenyl-2tf-l,4-benzodiazepin-2-one to produce the optically pure S enantiomer in 91% yield. Acylation with indole-2-carboxylic acid produced L-364,718, an extremely potent nonpeptidal peripheral CCK antagonist. © 1987, American Chemical Society. All rights reserved.