Pyridine → HCID 15381194, compound

Participants

Reaction Steps

A solution of (R)-[[3-[3-fluoro-4-(3-methoxy-1-azetidinyl)phenyl]-2oxo-5-oxazolidinyl]methyl]azide (0.393 g, 1.22 mmol) in 5:1 methanol/dichloromethane (20 mL) was treated with 10% palladium on carbon (0.030 g) under a nitrogen stream. The atmosphere was then replaced with hydrogen (balloon). After stirring 3 hours under hydrogen, the reduction was judged to be complete by TLC analysis (5% methanol/chloroform). The reaction mixture was filtered through Celite® and concentrated under reduced pressure. The crude 5-(aminomethyl)oxazolidinone was dissolved in dichloromethane (15 mL) and treated with pyridine (0.118 mL, 1.46 mmol) and acetic anhydride (0.138 mL, 1.46 mmol) under a nitrogen atmosphere at ambient temperature. After 2 h, the reaction was judged to be complete by TLC. The reaction mixture was washed with water and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. Chromatography over silica gel (50 g), eluting with a gradient of 1-3% methanol/chloroform, afforded, after concentration of appropriate fractions, 0.281 g (68%) of the title antibacterial agent as a white solid. An analytical sample, prepared by recrystallization from 2:1 ethyl acetate/hexane, was a white solid with mp 160°-161.5° C. and MS(EI) 337 (M+).

Provenance & Evidence