Acetic Acid → Diphenylmethyl 7-Amino-3-(3-chloro-1-propen-1-yl)-3-cephem-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of XVII from Preparation No. 7 (180 mg, 0.34 mmole) in ethyl acetate (10 ml) was added to a solution of Girard Reagent T [(carboxymethyl)trimethylammonium chloride hydrazide] (251 mg, 1.5 mmole) in CH3OH (10 ml) containing acetic acid (0.25 ml), at 5° C. After stirring for 30 minutes at 5° C., the mixture was concentrated to remove the CH3OH and then ethyl acetate (20 ml) was added. The ethyl acetate solution was washed with H2O (2×5 ml), saturated aqueous NaHCO3 (5 ml) and brine (5 ml), successively and dried over MgSO4. Evaporation of the solvent gave 145 mg (97%) of the title compound XVIII (Z isomer) as a yellow powder. M.p. >100° C. (dec.).

Provenance & Evidence