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Synthesis of α,α-Difluoro-β-amino Esters or gem-Difluoro-β-lactams as Potential Metallocarboxypeptidase Inhibitors

✍ Scribed by Nicolas Boyer; Philippe Gloanec; Guillaume De Nanteuil; Philippe Jubault; Jean-Charles Quirion

Publisher: John Wiley and Sons
Year: 2008
Tongue: English
Weight: 437 KB
Volume: 2008
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.200800363

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✦ Synopsis

Abstract

The synthesis of gem‐difluorinated β‐lactams and gem‐difluorinated β‐amino acids, each possessing a potential basic functional group, from ethyl bromodifluoroacetate and either imines (for β‐lactams) or N‐(α‐aminoalkyl)benzotriazoles (for β‐amino esters) was investigated. A series of these compounds were used for the design of novel metallocarboxypeptidase inhibitors. N‐Alkylation and N‐acylation of these two versatile scaffolds were carried out, leading to the expected targets in moderate to good yields.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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