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A new titanate/(+)-(1R,2S)-cis-1-amino-2-indanol system for the asymmetric synthesis of (S)-tenatoprazole |
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| Authors: | Madeleine Delamare Sébastien Belot Frédéric Martinet Henri B Kagan |
| Institution: | a Activation S.A.S., 11 avenue Albert Einstein, 69100 Villeurbanne, France b Finorga, S.A., 497 route de Givors, BP9, 38670 Chasse-sur-Rhône, France c Negma-Lerads, Immeuble de Strasbourg, Avenue de l’Europe, Toussus le Noble, 78771 Magny les Hameaux Cedex, France d Laboratoire de Catalyse Moléculaire, Institut de Chimie Moléculaire et des Matériaux d’Orsay, UMR 8182, Université Paris-Sud, 91405 Orsay, France |
| Abstract: | Tenatoprazole, a substituted imidazopyridinyl derivative, is an irreversible proton pump inhibitor (PPI), which is used for the prevention and treatment of gastric acid-related diseases. A new highly efficient asymmetric oxidation using cumene hydroperoxide (CHP) as the oxidant in the presence of titanium tetraisopropoxide (Ti(OiPr)4) and (+)-(1R,2S)-cis-1-amino-2-indanol, in a polar aprotic solvent at 0-20 °C, has been developed to prepare tenatoprazole with an enantiomeric excess of >99%, a chemoselectivity of >90% and a chemical yield of >90% from the corresponding sulfide. This procedure was successfully implemented on scales ranging from 100 mg to multiple kilograms. Detailed studies of the parameters controlling purity and yield for this reaction are presented. |
| Keywords: | Tenatoprazole Enantioselective sulfoxidation cis-1-Amino-2-indanol Titanium alkoxide |
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