Deprotection of 4-Methoxybenzyloxycarbonyl Group with p-Toluenesulfonic Acid in Acetonitrile. Application to a Large-scale Preparation of 7-[d-2-Amino-2-(4-hydroxyphenyl)acetamido]cephalosporanic Acid

Abstract

The 4-methoxybenzyloxycarbonyl group of 7-[d-2-(4-hydroxyphenyl)-2-(4-methoxybenzyloxycarbonylamino)acetamido]cephalosporanic acid was effectively removed with p-toluenesulfonic acid in acetonitrile. The mechanism of the deprotection is discussed and the role of acetonitrile can reasonably be explained in terms of the Ritter reaction.