Sodium Azide → HCID 53639939, compound

Participants

Reaction Conditions

Reaction Steps

Crude (R)-[[3-[4-[3-[(tert-butyldimethylsilyl)oxy]-1-azetidinyl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]methanesulfonate (9.42 mmol) was dissolved in dry N,N-dimethylformamide (50 mL) and treated with sodium azide (4.42 g, 68.0 mmol) at ambient temperature. The reaction mixture was warmed to 65° C. under nitrogen for 4 h. TLC analysis (5% methanol/chloroform) at this time revealed the reaction to be complete. The reaction mire was diluted with ethyl acetate (100 mL) and washed with water (3×25 mL) and brine, dried over sodium sulfate, filtered and concentrated in vacuo to an amber solid. Chromatography over silica gel (125 g), eluting with a gradient of 10-20% ethyl acetate/hexane, afforded, after concentration of appropriate fractions, 2.21 g (56% for 3 steps) of the title azide as a white solid with mp 121°-122.5° C. and MS(EI) 421 (M+).

Provenance & Evidence