Water → (2S,3S)-3-Amino-2-methyl-4-oxo-1-azetidinesulfonic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 479 mg (0.001 mole) of (3S-trans)-3-methoxycarbonylamino-4-methyl-2-oxo-1-azetidinesulfonic acid, tetrabutylammonium salt in 10 ml of dichloromethane is treated with 139 μl of triethylamine and 112 μl of trichlorosilane. The resulting solution is refluxed for 3 hours and cooled to 0° C. Triethylamine (139 μl) and 0.5 ml of water are added, and the solution is stirred overnight. The resulting slurry is diluted with 20 ml of formic acid, stirred for 1 hour, and the solid filtered to give 117 mg of (3S-trans)-3-amino-4-methyl-2-oxo-1-azetidinesulfonic acid, inner salt.

Provenance & Evidence