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Practical synthesis and regioselective alkylation of methyl-4(5)-(pentafluoroethyl)-2-propylimidazole-5(4)-carboxylate to give DuP 532, a potent angiotensin II antagonist



Practical synthesis and regioselective alkylation of methyl-4(5)-(pentafluoroethyl)-2-propylimidazole-5(4)-carboxylate to give DuP 532, a potent angiotensin II antagonist



Journal of Organic Chemistry 58(17): 4642-4645



DuP 532 (2), which is a potent angiotensin II receptor antagonist, has been prepared by two different routes. One route, which is more practical for large-scale synthesis, required the preparation of methyl 4(5)-(pentafluoroethyl)-2-propylimidazole-5(4)-carboxylate (9). This imidazole was synthesized in five steps from commercially available 11 in 32% overall yield. Alternate perfluoroalkylation methods of the iodoimidazole precursor 14 are presented.

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