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Griffiths GJ, Hauck MB, Imwinkelried R, et al. Novel Syntheses of 2-Butyl-5-chloro-3H-imidazole-4-carbaldehyde: A Key Intermediate for the Synthesis of the Angiotensin II Antagonist Losartan. J Org Chem. 1999;64(22):8084-8089doi: 10.1021/jo9824910.
Griffiths, G. J., Hauck, M. B., Imwinkelried, R., Kohr, J., Roten, C. A., Stucky, G. C., & Gosteli, J. (1999). Novel Syntheses of 2-Butyl-5-chloro-3H-imidazole-4-carbaldehyde: A Key Intermediate for the Synthesis of the Angiotensin II Antagonist Losartan. The Journal of organic chemistry, 64(22), 8084-8089. https://doi.org/10.1021/jo9824910
Griffiths, Gareth J., et al. "Novel Syntheses of 2-Butyl-5-chloro-3H-imidazole-4-carbaldehyde: A Key Intermediate for the Synthesis of the Angiotensin II Antagonist Losartan." The Journal of organic chemistry vol. 64,22 (1999): 8084-8089. doi: https://doi.org/10.1021/jo9824910
Griffiths GJ, Hauck MB, Imwinkelried R, Kohr J, Roten CA, Stucky GC, Gosteli J. Novel Syntheses of 2-Butyl-5-chloro-3H-imidazole-4-carbaldehyde: A Key Intermediate for the Synthesis of the Angiotensin II Antagonist Losartan. J Org Chem. 1999 Oct 29;64(22):8084-8089. doi: 10.1021/jo9824910. PMID: 11674720.
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J Org Chem. 1999 Oct 29;64(22):8084-8089. doi: 10.1021/jo9824910.

Novel Syntheses of 2-Butyl-5-chloro-3H-imidazole-4-carbaldehyde: A Key Intermediate for the Synthesis of the Angiotensin II Antagonist Losartan.

The Journal of organic chemistry

Gareth J. Griffiths, Michael B. Hauck, René Imwinkelried, Jörg Kohr, Conrad A. Roten, Gerhard C. Stucky, Jacques Gosteli

Affiliations

  1. Cerecon AG, Hauptstrasse 144, CH-4416, Bubendorf, Switzerland.

PMID: 11674720 DOI: 10.1021/jo9824910

Abstract

Reaction of glycine methyl ester (19) with imidate 18 under carefully optimized conditions allowed preparation of the rather unstable imidazolinone 11 in ca. 90% yield. Reaction of 11 with POCl(3)/DMF followed by aqueous workup gave aldehyde 2, a key intermediate for the synthesis of the angiotensin II antagonist Losartan, in ca. 55% yield. Structural identification of intermediates and byproducts formed during both the reaction to prepare 11 and the reaction of 11 with POCl(3)/DMF allowed development of several closely related syntheses of aldehyde 2.

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