Efficient and Scalable Synthesis of Ketoprofen: A Pyrolytic Aromatization Approach,Organic Process Research & Development

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Efficient and Scalable Synthesis of Ketoprofen: A Pyrolytic Aromatization Approach
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2023-05-04 , DOI: 10.1021/acs.oprd.3c00049
Lili Song _{1,

2} , Zhigang Liu _{1,

2} , Minjie Liu _{1,

2} , Pei Tang ₃ , Fener Chen _{1,

2,

3}

Affiliation

The practical synthesis of the representative nonsteroidal anti-inflammatory drug ketoprofen has been accomplished in 44% overall yield on the decagram scale. The key features in this synthetic work involve a TiCl₄–Et₃N mediated aldol/enol-lactonization annulation to affect dihydrobenzofuranone core formation and the use of a highly efficient pyrolytic aromatization condition to facilitate the construction of the vital 2-arylpropionic acid (2-APA) moiety. Furthermore, the avoidance of hazardous chemicals and crystallization of several intermediates would be greatly beneficial to the scalable synthesis of ketoprofen.

中文翻译：

酮洛芬的高效和可扩展合成：一种热解芳构化方法

代表性非甾体类抗炎药酮洛芬的实际合成已实现，十克级总收率为 44%。这项合成工作的关键特征包括 TiCl ₄ –Et ₃ N 介导的醛醇/烯醇内酯化环化影响二氢苯并呋喃酮核心形成，并使用高效热解芳构化条件促进重要的 2-芳基丙酸的构建 (2 -APA) 部分。此外，避免危险化学品和几种中间体的结晶将非常有利于酮洛芬的可扩展合成。

更新日期：2023-05-04

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