tert-Butyl bromoacetate → (S)-N-[[3-[[(t-Butyloxy)carbonyl]amino]-2-oxo-1-azetidinyl]carbonyl]glycine, t-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a suspension of potassium cyanate (933 mg, 11.5 mmol) in 10 ml of dimethylformamide was added t-butyl bromoacetate (1.8 ml, 11 mmol). The mixture was heated to 100° C. for 1 hour and cooled to room temperature. (S)-3-[[(t-Butyloxy)carbonyl]amino]-2-azetidinone (1.860 g, 10 mmol) was then added, and the mixture was heated to 65° C. After being stirred at 65° C. for 1 hour, the mixture was heated to 100° C. and stirred for an additional hour. Additional isocyanate was prepared (using 933 mg of potassium cyanate and 1.8 ml of t-butyl bromoacetate as described above) and added to the reaction mixture at room temperature. After being heated at 65° C. for 1 hour and 100° C. for 1 hour, the reaction mixture was stirred at room temperature overnight.

Provenance & Evidence