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Synfacts 2013; 9(1): 0006
DOI: 10.1055/s-0032-1317726
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Candesartan Cilexetil

Contributor(s):
Philip Kocienski
Seki M * Mitsubishi Tanabe Pharma Corporation, Osaka, Japan
An Efficient C–H Arylation of a 5-Phenyl-1H-tetrazole Derivative: A Practical Synthesis of an Angiotensin II Receptor Blocker.

Synthesis 2012;
44: 3231-3237
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Further Information

Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

candesartan cilexetil - angiotensin II receptor antagonists - C–H arylation - ruthenium - transfer hydrogenation

Significance

Candesartan cilexetil (Atacand®) is an angiotensin II receptor antagonist that is prescribed for the treatment of hypertension. It is a prodrug that is hydrolyzed to candesartan in the gut. The synthesis depicted, features an efficient protocol for ruthenium-catalyzed C–H arylation of the tetrazole A.


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Comment

A significant challenge in this small-scale synthesis was the final removal of the benzyl protecting group from the tetrazole unit using transfer hydrogenation. Best results were obtained using a ‘thickshell’ Pd/C catalyst from Evonik.


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