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

J Org Chem

Department of Process Research, Merck Research Laboratories, P.O. Box 2000, Rahway, New Jersey 07065, USA.

Published: July 2002

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.

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http://dx.doi.org/10.1021/jo011170cDOI Listing

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