Atliprofen methyl ester, IDPH-8261
2-(4-噻吩-3-基-苯基)-丙酸 2-(4-(3-噻吩)苯基)丙酸甲酯Chemical Name: 2-[4-(3-Thienyl)phenyl]propionic acid methyl ester
CAS No. 108912-17-0, 108912-14-7 (free acid), 158885-09-7 (racemic free acid)
项目整合开发状态: Phase III
项目研究机构: Indian Drugs (Originator)
合成路线:The reaction of 3 p-tolylthiophene (I) with N-bromosuccinimide in refluxing CCl4 in the presence of azobisisobutyronitrile or benzoyl peroxide as catalyst gives 4-(3-thienyl)benzyl bromide (II),which is converted to 4-(3-thienyl)phenylacetonitrile (III) by treatment with NaCN in refluxing dichloroethane using tetrabutyl ammonium hydrogen sulfate as catalyst Methylation of nitrile (III) with methyl iodide dimethylcarbonate in the presence of sodium methoxide,followed by acid hydrolysis of the resulting 4-(3-thienyl)phenyl-alpha-methylacetonitrile (IV) by refluxing with acetic acid hydrochloric acid (V),gives 4 (3-thienyl)phenyl-alpha-methylacetic acid (V),which is finally esterified by refluxing with CH3OH - H2SO4 to give IDPH-8261.
📌 参考资料/链接：
参考文献标题:4-(3-Thienyl)phenylalkanoic acid derivs.
文献作者:Marwah,A.; Sastry,C.V.R.; Shridhar,D.R.(Indian Drugs & Pharmaceuticals Ltd.)
参考来源:DE 3537768
📄 详细内容
合成路线:The reaction of 3 p-tolylthiophene (I) with N-bromosuccinimide in refluxing CCl4 in the presence of azobisisobutyronitrile or benzoyl peroxide as catalyst gives 4-(3-thienyl)benzyl bromide (II),which is converted to 4-(3-thienyl)phenylacetonitrile (III) by treatment with NaCN in refluxing dichloroethane using tetrabutyl ammonium hydrogen sulfate as catalyst Methylation of nitrile (III) with methyl iodide dimethylcarbonate in the presence of sodium methoxide,followed by acid hydrolysis of the resulting 4-(3-thienyl)phenyl-alpha-methylacetonitrile (IV) by refluxing with acetic acid hydrochloric acid (V),gives 4 (3-thienyl)phenyl-alpha-methylacetic acid (V),which is finally esterified by refluxing with CH3OH - H2SO4 to give IDPH-8261.
参考文献标题:IDPH-8261
文献作者:Arya,V.P.
参考来源:Drugs Fut 1988,13(5),411
产品链接: CAS No.108912-14-7›› 产品链接: CAS No.158885-09-7››