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

Paul J. Reider, Paul Davis, David L. Hughes, Edward J.J. Grabowski

Research output: Contribution to journalLetter

89 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)955-957
Number of pages3
JournalJournal of Organic Chemistry
Volume52
Issue number5
DOIs
StatePublished - Mar 1 1987
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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