Synthesis of Esomeprazole through Asymmetric Oxidation

Abstract:

N, N'-dicyclohexyl-D-tartaric diamide 2a and N, N'-di-[(R)-inda-D-tartaric diamide 2b were prepared through the reaction of diethyl-D-tartrate with cyclohexylamine and (R)-(-)-1-aminoindan, respectively. The two compounds coordinated with isopropyl titanate (Ti (O-iPr)₄), were used as catalyst in the asymmetric oxidation of pyrmetazol 3 with cumene hydroperoxide (CHP) as oxidant. The results revealed that both the catalytic systems derived from ligand 2a and 2b with Ti (O-iPr)₄ showed good catalytic activity and enantioselectivity in the synthesis of esomeprazole. Under the optimized conditions, the yield reached 91%, 91% and the enantio excess (ee) was up to 87% , 89%.

• Periodical: Advanced Materials Research (Volumes 881-883)
• Pages: 351-355
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.881-883.351
• Online since: January 2014
• Authors: Zhi Cheng Li*, Xiao Bo Kong, Wen Peng Mai, Gang Chun Sun, Shi Zhao Zhao
• Keywords: Asymmetric Oxidation, D-Tartaric Diamide, Esomeprazole

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