Synthesis of a 5-((Aryloxy)methyl)-3-(4-(trifluoromethyl)phenyl)[1,2,4]thiadiazole Derivative: A Promising PPARα,δ Agonist

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• 作者：Michael Reuman ; Zhiyong Hu ; Gee-Hong Kuo ; Xun Li ; Ronald K. Russell ; Lan Shen ; Scott Youells ; Yongzheng Zhang
• 刊名：Organic Process Research & Development
• 出版年：2007
• 出版时间：November 2007
• 年：2007
• 卷：11
• 期：6
• 页码：1010 - 1014
• 全文大小：122K
• 年卷期：v.11,no.6(November 2007)
• ISSN：1520-586X

文摘

The preparation of the PPARα,δ agonist 2-methyl-2-(2-methyl-4-(3-(4-(trifluoromethyl)phenyl)[1,2,4]thiadiazol-5-ylmethoxy)phenoxy)propionic acid sodium salt (17) is described and compared with earlier in-house preparations of this important target compound. Key concerns around a large-scale synthesis of this thiadiazole derivative were a large number of purification steps, the use of dichlorobenzene as a solvent, and a possible large-scale Baeyer–Villiger oxidation. This paper describes a straightforward preparation of the target agonist using methylhydroquinone (MHQ) as an inexpensive precursor that eliminates the need of an oxidation step.