Hydrochloric Acid → HCID 178477370, compound

Participants

Reaction Steps

A solution of diphenylmethyl 3-bromomethyl-7β-(2-thienylacetamido)-ceph-3-em-4-carboxylate (17.505 g.) and 5-mercapto-1-methyltetrazole (3.486 g.) in dry tetrahydrofuran (250 ml.) was stirred at 10° and treated, over 5 minutes, with a solution of triethylamine (4.16 ml.) in dry tetrahydrofuran (50 ml.). The resulting suspension was stirred for a further 45 minutes (during which time the temperature was allowed to rise to ca. 20°) and then added, over 5 minutes, to a stirred mixture of 2 N-hydrochloric acid (50 ml.), water (700 ml.), brine (700 ml.), and ethyl acetate (1.5 l.). The organic phase was separated, washed with 2 N-hydrochloric acid, water and brine, treated with some charcoal and filtered through a pad of kieselguhr. The filtrate was dried and evaporated to a foam (20.6 g.). This foam was dissolved in hot methanol (200 ml.), and the solution cooled to give the ester as colourless plates (14.391 g., 77.5%), λmax. (EtOH) 264 nm, (ε8,700), νmax. (CHBr3) 3420 (NH), 1780 (β-lactam), 1710 (CO2R), and 1680 and 1502 cm.-1 (CONH), τ (CDCl3) values include 3.40 (NH, doublet, J 9 Hz.), (C.7 H, double doublet, J 5 and 9 Hz.), 5.02 (C-6 H, doublet, J 5 Hz.), 6.19 (CH3).

Provenance & Evidence