Development of a Practical and Convergent Process for the Preparation of Sulopenem

Autor:	Jade D. Nelson, Handfield Robert Eugene, Nathan D. Ide, Hahdi H. Perfect, Esmort Chisowa, Mark P. Delude, Marcus Ewing, Durgesh V. Nadkarni, R. Matt Weekly, Mark Olivier, John J. Teixeira, Steven J. Brenek, John P. Zelina, James E. Phillips, Michele T. Drexler, Stephane Caron
Rok vydání:	2012
Předmět:	chemistry.chemical_compound chemistry Organic Chemistry Side chain Organic chemistry Regioselectivity Sulfoxide Physical and Theoretical Chemistry Combinatorial chemistry
Zdroj:	Organic Process Research & Development. 16:1348-1359
ISSN:	1520-586X 1083-6160
Popis:	Previous synthetic processes for the preparation of sulopenem involved multistep linear sequences in which the chiral sulfoxide side chain was introduced early in the process. This contribution summarizes the development of a practical and convergent process for the large-scale preparation of 1. The key step in the synthesis involves cyclization of an oxalimide intermediate to provide the thiopenem core. This convergent strategy allows for late introduction of the expensive and labile chiral sulfoxide subunit. Additionally, a regioselective sulfur oxidation and an improved deprotection sequence were developed. The latter provides API of high purity without the need for recrystallization.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::27868eef6640fda5cc31ed01a3b68a74 https://doi.org/10.1021/op300131e Zobrazit plný text záznamu