1,8-Diazabicyclo(5.4.0)undec-7-ene → N-[(5S)-3-(3-Fluoro-4-(4-azidomethylimidazol-1-yl)phenyl)-2-oxooxazolidin-5-yl-methyl]acetamide

Participants

Reaction Steps

N-[(5 S)-3-(3-Fluoro-4-(4-hydroxymethylimidazol-1-yl)phenyl)-2-oxooxazolidin-5-yl-methyl]acetamide (1.74 g, 5 mM) was suspended in dry dichloromethane (60 ml), diphenylphosphoryl azide (2.47 g, 9 mM) and 1,8-diazabicyclo[5.4.0]undec-7-ene (1.82 g, 12 mM) added, and the mixture stirred under argon at ambient temperature for 48 hours. The resulting solution was columned on silica (75 g) through a sinter funnel, eluting with a gradient increasing in polarity from 0 to 10% methanol in dichloromethane. Relevant fractions were combined and evaporated to give the title product (1.76 g).

Provenance & Evidence