Article title: Synthesis and characterization of four diastereomers of β-lactamase inhibitor drug intermediate
Authors: Amit Pund, Aniruddha Varangaonkar, Vipul Rane, Vinod Ahirrao, Mohammad Rafeeq, Ravindra Yeole, and Arvind Merwade
Journal: LSYC: Synthetic Communications
DOI: https://doi.org/10.1080/00397911.2023.2290625
When this article was originally published online, abstract was not correctly included. The appropriate abstract is provided below.
Abstract:
A short and efficient stereo-specific synthesis of three stereoisomers (two diastereomer and one enantiomer) of Oxalate salt of benzyl (2S,5R)-5-(benzyloxyamino)piperidine-2-carboxylate (8) has been described. Compound 8 is a key intermediate in the synthesis of b-lactamase inhibitors, was synthesized in high diastereomeric excess using chirally pure L-pyroglutamic acid. In this report, we also describe a chiral high performance liquid chromatography (CHPLC) method to separate these isomers. The developed CHPLC method was validated for the accurate determination of the diastereomeric purity of compound 8.