Ethyl (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate oxalate

In this context, the compound provides the correctly configured piperidine core, in which the (2S,5R) stereochemistry is crucial for the biological activity of the final molecule. The benzyloxy-protected amino group serves as a temporary protecting group that can be selectively removed under controlled conditions to reveal the free amine for further functionalization. During the synthesis, this intermediate undergoes key transformations such as deprotection, acylation, and formation of the diazabicyclooctane (DBO) core, ultimately leading to the active avibactam structure. Its oxalate salt form enhances stability and handling during large-scale synthesis, making it suitable for pharmaceutical manufacturing processes. Ethyl (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate oxalate is an important chiral intermediate used in the multistep synthesis of avibactam, a non-β-lactam β-lactamase inhibitor.