Chlorotrimethylsilane → (3S-trans)-4-methyl-2-oxo-3-(phenylacetylamino)-1-azetidinesulfonic acid, tetrabutylammonium salt

Participants

Reaction Steps

A solution of 531 mg (0.001 mole) of (3S-trans)-4-methyl-2-oxo-3-(phenyloxycarbonylamino)-1-azetidinesulfonic acid, tetrabutylammonium salt, in 15 ml of 1,2-dichloroethane is refluxed for 90 minutes with 278 μl of triethylamine and 250 μl of trimethylchlorosilane. After distillation of 5 ml of solvent, a solution of 136 mg of phenylacetic acid and 140 μl of triethylamine in 1 ml of dimethylformamide is added and the mixture is refluxed for 2 hours. The reaction mixture is poured into water and extracted into dichloromethane. After washing with saturated sodium bicarbonate solution, the organic layer is dried and evaporated. Trituration with ether gives 239 mg of (3S-trans)-4-methyl-2-oxo-3-(phenylacetylamino)-1-azetidinesulfonic acid, tetrabutylammonium salt.

Provenance & Evidence