Efficient one-pot synthesis of the 2-aminocarbonylpyrrolidin-4-ylthio-containing side chain of the new broad-spectrum carbapenem antibiotic ertapenem

Karel M.J. Brands, Ronald B. Jobson, Karen M. Conrad, J. Michael Williams, Brenda Pipik, Mark Cameron, Antony J. Davies, Peter G. Houghton, Michael S. Ashwood, Ian F. Cottrell, Robert A. Reamer, Derek J. Kennedy, Ulf H. Dolling, Paul J. Reider

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28 Scopus citations

Abstract

An efficient synthesis of the 2-aminocarbonylpyrrolidin-4-ylthio containing side chain of ertapenem (MK-0826) is described. Starting material N-(O,O-diisopropyl phosphoryl)-trans-4-hydroxy-L-proline is converted in a one-pot process to (2S)-cis-3-[[(4-mercapto-2-pyrrolidinyl)carbonyl]amino]benzoic acid monohydrochloride in 70-75% overall yield via a series of six reactions. The development of each of these reactions and the isolation of the product is discussed in detail.

Original languageEnglish (US)
Pages (from-to)4771-4776
Number of pages6
JournalJournal of Organic Chemistry
Volume67
Issue number14
DOIs
StatePublished - Jul 12 2002
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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