Dicyclohexylcarbodiimide → HCID 15017682, compound

Participants

Reaction Steps

To a mixture of (Z)-2-(tritylaminothiazol-4-yl)-2-acetoxyiminoacetic acid (1.95 g, 4.0 mmol) and 1-hydroxybenzotriazole (600 mg, 4.0 mmol) in THF (14 ml) was added DCC (824 mg, 4.0 mmol) and the mixture was stirred for 1 hr in an ice bath. Diphenylmethyl 7-amino-3-[(Z)-3-acetoxy-1-propenyl]-3-cephem-4-carboxylate (1.30 g, 2.8 mmol) was added to the suspension and the mixture was stirred for 4 hrs at ambient temperature, filterd, and diluted with AcOEt (60 ml). The organic phase was washed with water, dried over MgSO4, and concentrated under reduced pressure. The residue was chromatographed on a column of silica gel (Wakogel C200, 80 g), which was eluted with toluene-AcOEt (6:1). Fractions which contained the product were combined and concentrated in vacuo to give 2.01 g (77%) of diphenylmethyl 7-[(Z)-2-(tritylaminothiazol-4-yl)-2-acetoxyiminoacetamido]-3-[(Z)-3-acetoxy-1-propenyl)-3-cephem-4-carboxylate.

Provenance & Evidence