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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.

SUBMITTER: Yari A

PROVIDER: S-EPMC6648569 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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

Yari Ahmad A Zolali Amin A Karimian Khashayar K

ACS omega 20190109 1

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. ...[more]

PMID: 31459358

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