Bromhydrol → 2,2,2-Trichloroethyl 2-methyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate

Participants

Reaction Steps

A solution of aluminum bromide (3.4 g.) in dried dichloromethane (20 ml.) was dropwise added at -10° C. over about 10 minutes to a solution of 2,2,2-trichloroethyl 2-methyl-2,3-methylene-6-(2-phenylacetamido)penam-3-carboxylate (4.6 g.) in dried dichloromethane (30 ml.). After addition, the reaction mixture was stirred for 4.5 hours at room temperature, washed in turn with 2% hydrochloric acid (30 ml.) three times, a saturated sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution. After drying over magnesium sulfate, the solvent was distilled off and the residue was washed with ether and collected by filtration to give 2,2,2-trichloroethyl 2-methyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate (3.3 g.). This compound was recrystallized from ethanol to give crystals, mp 175° to 178° C.

Provenance & Evidence