Sodium Azide → (2S,4S)-4-acetylthio-2-(4-azidomethylthiazol-2-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Participants

Reaction Conditions

Reaction Steps

To a solution of (2S,4S)-4-acetylthio-2-[4-(methanesulfonyloxymethyl) thiazol-2-yl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.5 g) in dimethylformamide (20 ml) was added sodium azide (0.15 g) at ambient temperature. After stirring at 70° C. for 2 hours, the mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and brine successively, dried over magnesium sulfate and concentrated to give a syrup. The syrup was subjected to a column chromatography on silica gel and eluted with a mixture of acetone and dichloromethane (1:9, V/V) to give (2S, 4S)-4-acetylthio-2-(4-azidomethylthiazol-2-yl) -1-(4-nitrobenzyloxycarbonyl)pyrrolidine (500 mg).

Provenance & Evidence