PROCESS FOR THE PREPARATION OF CHIRAL TERT-BUTYL 4-((1R,2S,5R)-6-(BENZYLOXY)-7-OXO-1,6-DIAZABICYCLO3.2.1OCTANE-2-CARBOXAMIDO)PIPERIDINE-1-CARBOXYLATE DERIVATIVES AND (2S,5R)-7-OXO-N-PIPERIDIN-4-YL-6-(SULFOXY)-1,6-DIAZABICYCLO3.2.1OCTANE-2-CARBOXAMIDE

摘要

A process for the preparation of N-protected 6-(piperidin-4-ylcarbamoyl)piperidin-3-yl sulfonates of Formula (III): which comprises contacting a lactone of Formula (II): with an azacycloalkylamine of formula (II-Am): followed by contact with a sulfonyl halide of formula (II-Su): R⁴—SO₂W (II-Su) in the presence of tertiary amine base, wherein P^G1 and P^G2 are amine protective groups; k, p and q are 0, 1, or 2, and W, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, and R⁹ are defined herein. Additional embodiments add a series of process steps leading to the synthesis of 7-oxo-1,6-diazabicyclo[3.2.1]octanes suitable for use as β-lactamase inhibitors.;