Chloroacetyl isocyanate → Benzhydryl (E)-(2S,3S,5R)-3-[3-(2-chloro-acetylamino-carbonyloxy)-propenyl]-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

Participants

Reaction Steps

300 mg (0.73 mmol) of benzhydryl (E)-(2S,3S,5R)-3-(3-hydroxy- propenyl)-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate were dissolved in 10 ml of tetrahydrofuran under argon and treated with 90 μl (1.05 mmol) of chloroacetyl isocyanate. The mixture was stirred for 3 hours, evaporated and chromatography was carried out over silica gel (particle size 0.040-0.063 mm) with ethyl acetate:n-hexane (9:16) as the eluent. Yield: 300 mg (77%) of colorless foam IR (KBr): 3300(br), 1779, 1753, 1730, 1495, 1203 cm-1MS: (M+NH4)+ 546.4

Provenance & Evidence