Tuesday, 24 May 2005 - 9:35 AM

This presentation is part of: Green Chemistry I

Development of an environmentally sound process for production of the new carbapenem antibiotic ertapenem sodium

J. Michael Williams, Merck Research Laboratories, Rahway, NJ

INVANZ is a new carbapenem antibiotic developed at Merck for treatment of serious bacterial infections. Ertapenem sodium, the active ingredient, is unstable in solution presenting a difficult challenge for development of an environmentally responsible manufacturing process. Our strategy led to an efficient, environmentally sound process that is now used in the commercial production of INVANZ for sale worldwide. Innovative chemical reactions and a novel method for improving product stability served to reduce the burden on purification. A highly selective low temperature reaction is used in assembly of the carbapenem. Hydrogenolysis of a p-nitrobenzyl ester gives ertapenem in 90% yield for two steps. Use of bicarbonate was key in improving reaction performance and stability of the product through formation of the sodium carbamate. An extraction makes use of a reaction by-product as an ion-pairing agent simultaneously purifying and concentrating the aqueous product stream. Crystallization affords 65% overall yield of ertapenem sodium.

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