Sodium Azide → HCID 15381193, compound

Participants

Reaction Conditions

Reaction Steps

(R)-[[3-[3-fluoro-4-(3-methoxy-1-azetidinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]methanesulfonate (0.508 g, 1.36 mmol) was combined with sodium azide (0.106 g, 1.63 mmol) in N,N-dimethylformamide (4 mL). The reaction mixture was heated to 65° C. under a nitrogen atmosphere. After 2 hours, a small amount of the starting mesylate still remained by TLC analysis (5% methanol/chloroform). An additional 0.044 g of sodium azide was added and the reaction heated for a further 1.5 h, at which time TLC revealed the reaction to be complete. The reaction mixture was filtered and concentrated in vacuo. The residue was chromatographed over silica gel (25 g), eluting with a gradient of 1-3% methanol/chloroform. Appropriate fractions were combined and concentrated in vacuo to furnish 0.426 g (98%) of the title compound as an off-white solid. An analytical sample was prepared by recrystallization of this material from 3:1 ethyl acetate/hexane to give a white solid with mp 111°-112.5° C. and MS(EI) 321 (M+).

Provenance & Evidence