Pyridine → HCID 53806064, compound

Participants

Reaction Steps

A solution of (R)-[[3-[4-[(1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]azide (0.652 g, 1.96 mmol) in MeOH (20 mL) and CH2Cl2 (10 mL) was treated with 10% palladium/carbon (0.095 g) under a N2 stream. The atmosphere was then replaced with H2 (balloon) by repeated evacuation and filling and the mixture stirred at ambient temperature under H2. After 3 h, TLC analysis (5% MeOH/CHCl3) revealed the reduction to be complete. The reaction mixture was filtered through Celite® and the filtrate concentrated under reduced pressure. The crude 5-(aminomethyl)oxazolidinone was dissolved in CH2C2 (20 mL) and treated with pyridine (0.190 mL, 2.35 mmol) and then acetic anhydride (0.222 mL, 2.35 mmol). After 0.5 h, TLC analysis (5% MeOH/CHCl3) indicated the acetylation to be complete. The reaction mixture was washed with H2O and brine, dried over Na2SO4, filtered and concentrated in vacuo to give an off-white solid. Chromatography over silica gel (70 g), eluting with a gradient of 1-3% MeOH/CHCl3, afforded, after concentration of appropriate fractions, 0.517 g (76%) of the title oxazolidinone antibacterial agent as a white solid with mp 60-65° C. and MS(EI) 349 (M+).

Provenance & Evidence