On the Mechanism of Formation and the Synthesis of Pantoprazole Sodium Sesquihydrate-Related Compound E: A Phantom Chemical Entity

Abstract

A mechanism for the formation of pantoprazole related compound E (RC E) is proposed involving the formation of a radical cation in the pH range of 5-8. pH dependence of RC E is demonstrated, and the contribution of the difluoromethoxy group in stabilizing the C-6 free radical, a prerequisite to the formation of the dimer byproduct, is discussed. Also, the synthesis of pantoprazole RC E is reported using the benzidine rearrangement.