Tetrahydrofuran → HCID 54109413, compound

Participants

Reaction Steps

A tetrahydrofuran solution (5 ml) containing triethylamine (1.02 g) was added to a tetrahydrofuran solution (40 ml) containing 1-(1-carboxy-2-methylpropyl)-3-(2-phenylacetamido)-2-azetidinone (3.04 g) at -20° C. with stirring. To this solution, there was dropwise added a tetrahydrofuran solution (5 ml) containing ethyl chloroformate (1.14 g) at -10° C. in the course of 5 minutes, whereafter the mixture was stirred at -10° to 0° C. for 2 hours. To the resultant mixture, there was all at once added water (8 ml), in which sodium azide (1.23 g) was dissolved at the same temperature, and the stirring was continued for additional half an hour. The reaction mixture was poured into ice-water (200 ml) and the resultant mixture was extracted with three portions of 100 ml methylene chloride. The extracts were washed with three portions of 100 ml water and dried over calcium chloride. The solution was evaporated to dryness under reduced pressure to give oily 1-(1-azidocarbonyl-2-methylpropyl)-3-(2-phenylacetamido)-2-azetidinone (3.0 g).

Provenance & Evidence