Efficient Synthesis of Losartan, A Nonpeptide Angiotensin II Receptor Antagonist

Robert D. Larsen, Anthony O. King, Cheng Y. Chen, Edward G. Corley, Bruce S. Foster, F. Edward Roberts, Chunhua Yang, David R. Lieberman, Robert A. Reamer, David M. Tschaen, Thomas R. Verhoeven, Paul J. Reider, S. Lo Young, Lucius T. Rossano, Sidney Brookes, David Meloni, James R. Moore, John F. Arnett

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Abstract

A highly efficient, convergent approach to the synthesis of the angiotensin II receptor antagonist losartan (1) is described. Directed ortho-metalation of 2-trityl-5-phenyltetrazole provides the key boronic acid intermediate 10 for palladium-catalyzed biaryl coupling with bromide 5 obtained from the regioselective alkylation of the chloroimidazole 2. This methodology overcomes many of the drawbacks associated with previously reported syntheses.

Original languageEnglish (US)
Pages (from-to)6391-6394
Number of pages4
JournalJournal of Organic Chemistry
Volume59
Issue number21
DOIs
StatePublished - Oct 1 1994
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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    Larsen, R. D., King, A. O., Chen, C. Y., Corley, E. G., Foster, B. S., Roberts, F. E., Yang, C., Lieberman, D. R., Reamer, R. A., Tschaen, D. M., Verhoeven, T. R., Reider, P. J., Young, S. L., Rossano, L. T., Brookes, S., Meloni, D., Moore, J. R., & Arnett, J. F. (1994). Efficient Synthesis of Losartan, A Nonpeptide Angiotensin II Receptor Antagonist. Journal of Organic Chemistry, 59(21), 6391-6394. https://doi.org/10.1021/jo00100a048