p-Toluenesulfonic acid → N-[3-(t butyloxycarbonylamino)benzoyl]glycine benzyl ester

Participants

Reaction Conditions

Reaction Steps

Cyanomethyl 3-(t-butyloxycarbonylamino)-benzoate [compound of Example 61-(2)] (27.6 g), glycine benzyl ester.p-toluenesulfonate (33.7 g), triethylamine (20.2 g) and 4-dimethylaminopyridine (0.2 g) are mixed. The mixture is stirred at 80° C. two nights. The reaction mixture is extracted with ethyl acetate (200 ml). The extract is washed with water, and ethyl acetate is distilled off under reduced pressure. The residue is purified by a silica gel column chromatography (eluant, chloroform-ethyl acetate). The fractions containing the desired compound are collected, and the solvent is distilled off under reduced pressure. The residue is recrystallized from 70% aqueous acetonitrile to give N-[3-(t butyloxycarbonylamino)benzoyl]glycine benzyl ester (7.2 g). m.p.: 171°-173° C. (colorless needles) IR (KBr; cm-1): 1725, 1695, 1640

Provenance & Evidence