p-Nitrobenzyl 7alpha-azido-3-methanesulfonyloxy-3-acetoxymethyl-cepham-4-carboxylate → p-Nitrobenzyl 7alpha-azido-3-acetoxymethyl-ceph-3-em-4-carboxylate

Participants

Reaction Steps

A mixture of p-nitrobenzyl 7α-azido-3-methanesulfonyloxy-3-acetoxymethyl-cepham-4-carboxylate (0.72 g.), EM silica gel 60 (7.20 g.), and 3:1 PhH-EtOAc (20 ml.) is stirred in a stoppered flask for 4 days at room temperature. The mixture is filtered through a sintered glass funnel to remove the silica gel, which is washed with several portions of EtOAc. Evaporation of the filtrate and washings leaves an oil. This material is chromatographed on Baker silica gel using 9:1 φH-EtOAc as an eluting solvent, to provide p-nitrobenzyl 7α-azido-3-acetoxymethyl-ceph-3-em-4-carboxylate.

Provenance & Evidence