m-Chloroperbenzoic acid → HCID 57039536, compound

Participants

Reaction Steps

A solution of p-nitrobenzyl (5R,6S)-2-ethylthio-6-methoxy-pen-2-em-3-carboxylate (96 mg, 0.24 mmol) in anhydrous DMF (1.2 ml) is diluted with CH2Cl2 (2.4 ml) and cooled in an ice-bath. A solution of 85% m-chloroperoxybenzoic acid (51 mg, 0.25 mmol) in CH2Cl2 (1.2 ml) is added dropwise over 2 minutes to the cold, stirring solution. The resulting mixture is kept at 0° for 60 minutes, and then treated with excess Amberlyst-21 resin and stirred and additional 5 minutes. The mixture is filtered and the filtrate is diluted with CH2Cl2 and washed with 5 portions of H2O. The organic phase is dried over MgSO4, filtered, and evaporated under vacuum to give a crude residue of the title compound which is purified by rapid chromatography on silica gel.

Provenance & Evidence