{"title":"A novel approach for the synthesis of (S)-tolvaptan and (S)-desmethyltolvaptan","authors":"D.R. Adarsh , S. Prashanth , Allam Vinaykumar , B.V. Subba Reddy","doi":"10.1016/j.tetlet.2024.155245","DOIUrl":null,"url":null,"abstract":"<div><p>A novel and concise approach has been developed for the total synthesis of (<em>S</em>)<strong>-</strong>tolvaptan, which is used for the treatment of hyponatremia. The key intermediate, benzazepinone has been synthesized in three steps through <em>ortho</em>-acylation of <em>N</em>-Pivalamide protected aryl amine followed by an intramolecular haloamine cyclization. The total synthesis of (<em>S</em>)<strong>-</strong>tolvaptan from <em>p</em>-chloroaniline has been accomplished in seven steps with 43% overall yield.</p></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"148 ","pages":"Article 155245"},"PeriodicalIF":1.5000,"publicationDate":"2024-08-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S004040392400340X","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A novel and concise approach has been developed for the total synthesis of (S)-tolvaptan, which is used for the treatment of hyponatremia. The key intermediate, benzazepinone has been synthesized in three steps through ortho-acylation of N-Pivalamide protected aryl amine followed by an intramolecular haloamine cyclization. The total synthesis of (S)-tolvaptan from p-chloroaniline has been accomplished in seven steps with 43% overall yield.
期刊介绍：
Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.
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