HCID 10255782, compound → HCID 131710752, compound

Participants

Reaction Steps

A solution of 2-dichloroacetoxyimino-2-(thien-2-yl)acetyl chloride 0.585 g.) in ethyl acetate (5 ml.) was added to a stirred suspension of diphenylmethyl 7β-amino-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethylceph-3-em-4-carboxylate (1 g.) in ethyl acetate (10 ml.) and propylene oxide (1 ml.) at 20°. After 30 minutes all the solid had dissolved. The solution was washed with 2 N-hydrochloric acid, saturated sodium bicarbonate solution, water and brine, dried and concentrated to give crude diphenylmethyl 7β-[2-dichloroacetoxyimino-2-(thien-2-yl)acetamido]-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethylceph-3-em-4-carboxylate (syn-isomer) as a solvated foam (1.567 g.) λmax. (EtOH) 267.5 nm (E11 240), τ values (CDCl3) include 3.00 (singlet, --CHPh2), 3.75 (singlet; CHCl2) and 7.35 (singlet; CH3).

Provenance & Evidence