N-Acetyl-L-Cysteine → Tert-butyl 3-carbamimidoyl-3-(1,1-dimethylethylsulfinamido)azetidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of (R)-2-acetamido-3-mercaptopropanoic acid (N-acetylcycteine, 0.812 g, 4.98 mmol), tert-butyl 3-cyano-3-(1,1-dimethylethylsulfinamido)azetidine-1-carboxylate (1.5 g, 4.98 mmol), and ammonium acetate (1.918 g, 24.88 mmol) in MeOH (5 ml) in a 15 ml sealed tube was heated at 70° C. overnight. Analysis of the reaction mixture by LCMS showed 38% desired product with other impurities but no starting material present. The reaction mixture was used for the next step without workup.

Provenance & Evidence