Dimethylformamide → (5S)-5-(azidomethyl)-3-benzyl-1,3-oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

A 40 ml vial was charged with 3-benzyl-5-(chloromethyl)-1,3-oxazolidin-2-one (112 mg, 0.5 mmol, INTERMEDIATE 13), dimethylformamide (5 ml), and sodium azide (130 mg, 2 mmol). The mixture was heated to 120° C. for 15 h. The crude was applied to a pad of silica and washed with methanol (2×10 ml). The organics were pooled and concentrated to provide a residue. The title compound was isolated on silica gel eluting with a gradient of dichloromethane/methanol from 0% to 100% to provide 100 mg (86%) as a tan oil. Mass spectrum (ESI) 233.2 (M+1).

Provenance & Evidence