Synthesis of ABT-378, an HIV protease inhibitor candidate: avoiding the use of carbodiimides in a difficult peptide coupling

EJ Stoner, PJ Stengel, AJ Cooper

Index: Stoner, Eric J.; Stengel, Peter J.; Cooper, Arthur J. Organic Process Research and Development, 1999 , vol. 3, # 2 p. 145 - 148

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Citation Number: 10

Abstract

An alternative to carbodiimide-mediated peptide coupling protocols has been developed for a carboxylic acid prone to decomposition by polymerization. This method, involving the in situ generation of an acyl imidazolide, has been applied to the preparation of a lead clinical HIV protease inhibitor candidate, ABT-378. The nature of the polymerization and optimization of the new reaction conditions are presented.