Route Development and Multikilogram GMP Delivery of a Somatostatin Receptor Antagonist

…, MA Huffman, GW Stewart, E Cleator…

Index: Ruck, Rebecca T.; Huffman, Mark A.; Stewart, Gavin W.; Cleator, Ed; Kandur, Wynne V.; Kim, Mary M.; Zhao, Dalian Organic Process Research and Development, 2012 , vol. 16, # 8 p. 1329 - 1337

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Citation Number: 5

Abstract

Route development and demonstration on multikilogram scale for the first GMP delivery of MK-4256 are described. Key aspects of the convergent route include a regioselective green iodination, one-pot oxadiazole synthesis, and an efficient ketone Pictet–Spengler reaction with diastereomeric upgrade via crystallization to afford 6 kg of API. A recycle procedure augmented the yield of desired diastereomer in the Pictet–Spengler reaction from a ...