American Chemical Society
ao8b00845_si_001.pdf (4.17 MB)

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

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journal contribution
posted on 2019-01-09, 18:33 authored by Ahmad Yari, Amin Zolali, Khashayar Karimian
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.