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Millifluidics for Chemical Synthesis and Time-resolved Mechanistic Studies
Published on: November 27, 2013
On the Mechanism of Formation and the Synthesis of Pantoprazole Sodium Sesquihydrate-Related Compound E: A Phantom
Ahmad Yari1, Amin Zolali1, Khashayar Karimian1,2
1Andisheh Pharmaceutical Sciences R&D, Ajand Pharma Holding Inc., Yousefabad, Jahanara Avenue, 23rd Street No. 8, Tehran 1438933743, Iran.
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.
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