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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 17
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Original Articles

Succinct Synthesis of Bosentan Utilizing Glycol Mono-THP Ether

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Pages 2488-2493 | Received 18 Feb 2014, Published online: 01 Jul 2014
 

Abstract

A concise synthetic method for bosentan, a nonpeptide orally active dual endothelin (ET-1A/B) receptor antagonist used for the treatment of pulmonary artery hypertension (PAH), was developed. We developed a new succinct synthetic route for bosentan by employing an acid-labile tetrahydropyran (THP)–protected glycol. THP group is advantageous over the previously known protection groups used in bosentan synthesis in that it provides a clean and quantitative deprotection. Bosentan was constructed via two parallel reaction pathways, yet the better product yield was obtained from a pathway via 6. Deprotection of THP ether was achieved under a mild acidic condition to afford bosentan.

GRAPHICAL ABSTRACT

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