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Citation: WAN Huan, FANG Feng, DUAN Mei-Li, XU Xu, JI Ya-Fei. Synthesis of Omeprazole[J]. Chinese Journal of Applied Chemistry, ;2009, 26(2): 178-181. shu

Synthesis of Omeprazole

WAN Huan ^a ,
FANG Feng ^a ,
DUAN Mei-Li ^a ,
XU Xu ^b ,
JI Ya-Fei ^a,,

1.
a School of Pharmacy, East China University of Science and Technology, Shanghai 200237;
2.
b College of Chemical Engineering, East China University of Science and Technology, Shanghai 200237

Corresponding author: JI Ya-Fei,
Received Date: 25 January 2008
Available Online: 7 April 2008
Fund Project: 华东理工大学科研基金资助项目(YJ0142114) (YJ0142114)

A new synthetic procedure was designed for the preparation of omeprazole.A one-pot method was performed for the oxidation of 2,3,5-trimethylpyridine and the nitration of 2,3,5-dimethylpyridine-N-oxide to get 2,3,5-dimethyl-4-nitropyridine-N-oxide,which was directly chlorinated with trichloroisocyanuric acid to provide the key intermediate 2-chloromethyl-3,5-dimethyl-4-nitropyridine-N-oxide.The chloromethylnitropyridine was treated with 2-mercapto-5-methoxybenzimidazole in the presence of excess sodium methoxide to simultaneously carry out the condensation and the methoxylation to give 5-methoxy-2-[(4-methoxy-3,5-dimethylpyridinyl-N-oxide)-methylthio]-1H-benzimidazole,from which omeprazole was finally obtained via the deoxidization with phosphorus trichloride and the oxidation with sodium perborate in an overall yield of 48.7%.The structures of the intermediates and omeprazole were confirmed by ¹H NMR and MS.
- omeprazole,
- proton pump inhibitor,
- trichloroisocyanuric acid,
- sodium perborate tetrahydrate
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