A new and efficient synthesis of a beta-lactam that is an advanced precursor of inhibitors of thrombin and tryptase is reported. The reaction sequence is based on the use of an inexpensive enantiomerically pure starting material and is designed to allow access to both enantiomers of the target molecules by epimerization of a side-product obtained along the synthesis. An improved procedure for the epimerization step that takes advantage of the use of a polymer-supported and recyclable phase-transfer catalyst is described.

Efficient synthesis of an enantiopure beta-lactam as an advanced precursor of thrombin and tryptase inhibitors / R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, F. Maggioni, A. Puglisi. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 68:7(2003), pp. 2952-2955. [10.1021/jo020617u]

Efficient synthesis of an enantiopure beta-lactam as an advanced precursor of thrombin and tryptase inhibitors

R. Annunziata;M. Benaglia;M. Cinquini;F. Cozzi;A. Puglisi
2003

Abstract

A new and efficient synthesis of a beta-lactam that is an advanced precursor of inhibitors of thrombin and tryptase is reported. The reaction sequence is based on the use of an inexpensive enantiomerically pure starting material and is designed to allow access to both enantiomers of the target molecules by epimerization of a side-product obtained along the synthesis. An improved procedure for the epimerization step that takes advantage of the use of a polymer-supported and recyclable phase-transfer catalyst is described.
Settore CHIM/06 - Chimica Organica
JOURNAL OF ORGANIC CHEMISTRY
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/193743
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