Ethyl Acetate → N-(5S)-[3-(3-fluoro-4-{4-ethyl-3-oxopiperazin-1-yl}phenyl)-2-oxooxazolidin-5-ylmethyl]acetamide

Participants

Reaction Steps

(5R)-5-Azidomethyl-3-(3-fluoro-4-{4-ethyl-3-oxopiperazin-1-yl-}phenyl)oxazolidin-2-one (750 mg) was dissolved in a mixture of DMF (5 ml) and ethyl acetate (10 ml), and the solution purged with argon. Palladium (10% on carbon, 150 mg) was added, followed by acetic anhydride (0.4 ml) and the mixture stirred at ambient temperature under hydrogen confined in a balloon for 2 hours. The mixture was filtered through celite, evaporated to dryness, and chromatographed on silica, using as eluant a gradient increasing in polarity from 0 to 10% methanol in dichloromethane. Relevant fractions were combined and evaporated, and the residue purified by crystallisation from acetonitrile to give N-(5S)-[3-(3-fluoro-4-{4-ethyl-3-oxopiperazin-1-yl}phenyl)-2-oxooxazolidin-5-ylmethyl]acetamide (145 mg).

Provenance & Evidence