Synthesis and characterization of four diastereomers of β-lactamase inhibitor drug intermediate

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 β-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.

GRAPHICAL ABSTRACT

Keywords:

• β-lactamase inhibitors
• chiral HPLC
• DBO core
• stereoisomers
• manufacturing scale

View correction statement:

Correction

Acknowledgements

The authors are thankful to the management of Wockhardt Ltd. for supporting this work. Authors also acknowledge all the team members of chemical and analytical research development of Wockhardt Research Centre, Aurangabad for their support in conducting this research work.

Disclosure statement

The presented work is original research work of Wockhardt Limited and all the authors are employees of Wockhardt Limited.

Correction Statement

This article was originally published with errors, which have now been corrected in the online version. Please see Correction: https://doi.org/10.1080/00397911.2023.2296144