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

Abstract

AbstractThe 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)