Dicyclohexylcarbodiimide → HCID 16166029, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-hydroxybenzotriazole (223 mg, 1.44 mmol) and (Z)-2-(2-tritylaminothiazol-4-yl)-2-trityloxyiminoacetic acid (1.06 g, 1.44 mmol) in THF (14 ml) was added DCC (300 mg, 1.44 mmol) and the mixture was stirred for 1 hr at 5° C. Diphenylmethyl 7-amino-3-[(E)-acetoxy-1-propenyl]-3-cephem-4-carboxylate (670 mg, 1.44 mmol) was added to the mixture. After stirring for 4 hr at ambient temperature, the reaction mixture was filtered, diluted with ethyl acetate (50 ml) and washed with water. Concentration of the organic layer gave an oil, which was chromatographed on a column of silica gel. Elution with toluene-ethyl acetate (10:1) gave 1.607 g (99%) of diphenylmethyl 7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-[(E)-3-acetoxy-1-propenyl]-3-cephem-4-carboxylate as an amorphous powder. IR νmax (KBr) cm-1 1770, 1730. 1H NMR (CDCl3) δ 2.0 (3H, s, OAc), 3.33 (2H, s, 2-H), 4.54 (2H, ABq, CH2OAc), 5.04 (1H, d, J=5 Hz, 6-H), 6.0 (1H, m, vinyl-H), 6.02 (1H, dd, J=5 & 7 Hz, 7-H), 6.40 (1H, s, thiazole-H), 6.82 (1H, d, J=15 Hz, vinyl-H), 7.00 (1H, s, Ph2CH), 7.3 (25H, s, Ph).

Provenance & Evidence