Hydrochloric Acid → HCID 131710767, compound

Participants

Reaction Steps

To a solution of 3-acetoxymethyl-7β-(2-hydroxyimino-2-phenylacetamido)ceph-3-em-4-carboxylic acid ethyl acetate solvate (syn-isomer) (1.0 g.) in dimethylformamide (21 ml.) containing triethylamine (0.425 g) was added 2-chloroethylisocyanate (0.274 g.) and the mixture was stirred at room temperature for one hour. The reaction mixture was acidified (2 N hydrochloric acid) and extracted with ethyl acetate. The extracts were combined and extracted with saturated aqueous sodium bicarbonate. The combined aqueous extracts were acidified (2 N-hydrochloric acid) and extracted with ethyl acetate, dried, concentrated and added dropwise to petroleum with vigorous stirring. The precipitated solid was filtered, dissolved in ethyl acetate (10 ml.) and added dropwise to petroleum (300 ml.). The precipitate was filtered and dried giving the title acid (0.76 g; 74%), [α]D +28° (c 1.0 DMSO), λmax. (pH 6 phosphate buffer) 257.5 nm. (ε 20,780), νmax. (Nujol) 3270 (NH), 1780 (β-lactam), 1660 and 1520 cm.-1 (amide), τ (DMSO-d6) values include -0.10 (doublet, J 8 Hz; NH), 6.2-6.7 (multiplet; C-2 CH2 +--CH2CH2Cl), 7.95 (singlet; OCOCH3).

Provenance & Evidence