Water → 3-[3-Fluoro-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-5-(azidomethyl)oxazolidin-2-one

Participants

Reaction Steps

(5R)-3-[3-Fluoro-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-5-[(methanesulfonyl)methyl]-oxazolidin-2-one (Intermediate 24a) (5.432 g, 14.7 mmol), sodium azide (1.092 g, 16.6 mmol), and 18-crown-6 (0.069 g, 0.26 mmol) in dimethylformamide (15 mL) were heated to 90° C. for 3.75 hours. The reaction mixture was poured into water (200 ml) and extracted with dichloromethane (3×100 ml). The combined organic layers were washed once with brine, dried over MgSO4 and concentrated under vacuum. Chromatography on silica gel with 5% methanol in dichloromethane gave the title compound (3.7 g) as a colourless solid.

Provenance & Evidence