Dicyclohexylcarbodiimide → HCID 178442197, compound

Participants

Reaction Steps

A stirred solution of diphenylmethyl(6R,7R)-7-amino-3-[(E)-pent-1-en-3-ynyl]ceph-3-em-4-carboxylate, hydrochloride (432 mg) in tetrahydrofuran (10 ml) was treated with triethylamine (125 μl). (Z)-2-(Carbamoylmethoxyimino)-2-(2-tritylaminothiazol-4-yl)acetic acid (441 mg), 1-hydroxybenzotriazole hydrate (162 mg) and N,N'-dicyclohexylcarbodiimide (248 mg) were added in that order. After 3 h, the precipitated N,N'-dicyclohexylurea was filtered off, the filtrate evaporated and the residue purified by column chromatography (60 g silica gel). Elution with ethyl acetate:dichloromethane (1:3) gave the title compound as a foam (441 mg); νmax (CHBr3) 3500, 3398 (NH2 +NH), 2215 (C≡C), 1786 (β-lactam), 1722 (CO2R), 1682, 1528 cm-1 (CONH); τ(CDCl3) 4.24 (CH=CH--C≡C), 5.33 (OCH2CONH2), 6.48, 6.60 (2-CH2), 8.02 (C≡CCH 3).

Provenance & Evidence