Water → HCID 88783904, compound

Participants

Reaction Steps

A solution of diphenylmethyl 3-bromomethyl-7β-formamidoceph-3-em-4-carboxylate, 1β-oxide (5.0 g) in N,N-dimethylformamide (30 ml.) was treated with ethanethiolic acid (4.0 ml) and triethylamine (1.4 ml.) and the reaction stirred for 1.6 hr. at +19°. The yellow solution was poured into water (100 ml.) and ethyl acetate (100 ml.) and the resulting insoluble solid was collected, washed with ethyl acetate and dried in vacuo over phosphorus pentoxide, to give diphenylmethyl 3-acetylthiomethyl-7β-formamidoceph-3-em-4-carboxylate, 1β-oxide (2.422 g, 49%), mp 198°-199° (dec.), [α]D -60° (c 1.0, DMSO), λmax. (EtOH) 273 nm (ε 10,300), νmax. (CHBr3) 3430 (NH), 1803 (β-lactam) 1725 (CO2R), 1695, 1505 (CONH), 1042 cm.-1 (S→O) τ (DMSO-d6), 1.66 (d, J 9; NH), 1.78 (s; CHO), 2.59 (m, phenyl), 3.01 (s, CHPh2), 7.68 (s; SCH3).

Provenance & Evidence