网站主页>>>项目整合精选>>>项目整合精选>>>Zoliprofen, 156-S, 480156-S

Zoliprofen, 156-S, 480156-S

唑利洛芬Chemical Name: alpha-Methyl-4-(2-thiazolyloxy)benzeneacetic acid; 2-[4-(2-Thiazolyloxy)phenyl]propionic acid
CAS No. 56355-17-0
项目整合开发状态: Phase II
项目研究机构: Shionogi (Originator)
合成路线:The esterification of 4-hydroxyphenylacetic acid (I) with isopropanol and H2SO4 gives the corresponding isopropyl ester (II),which is then cyclocondensed with 1-isobutoxy-2-chloroethyl isothiocyanate (III) by means of K2CO3 in acetone yielding isopropyl 2-[4-(4-isobutoxy-2-thiazolin-2-yloxy) phenyl]acetate (IV).Elimination of isobutanol from (IV) by means of p-toluenesulfonic acid in hot DMF affords isopropyl 2-[4-(2-thiazolyloxy)phenyl] acetate (V),which is methylated with methyl bromide and KOH in DMF giving isopropyl 2-[4-(2-thiazo)yloxy)phenyl]propionate (VI).Finally,this compound is hydrolyzed with NaOH in aqueous methanol.
📌 参考资料/链接:
参考文献标题:Improved process for the production of 2-(4-(2-thiazolyloxy)phenyl)propionic acid
文献作者:Hamada,Y.; Ando,S.(Shionogi & Co.Ltd.)
参考来源:CA 1188699; EP 0088008; JP 58148870

📄 详细内容


合成路线:The condensation of 2-chlorothiazole (VII) with isopropyl 2-(4-hydroxyphenyl)propionate (VIII) by means of K2CO3 in DMF at 150 C gives (VI),previously obtained.

参考文献标题:Thiazole derivatives and the production thereof
文献作者:Maeda,R.; Hirose,K.(Shionogi & Co.Ltd.)
参考来源:CA 1051906; FR 2248835; GB 1481465


合成路线:The esterification of 4-hydroxyphenylacetic acid (I) with isopropanol and H2SO4 gives the corresponding isopropyl ester (II),which is then cyclocondensed with 1-isobutoxy-2-chloroethyl isothiocyanate (III) by means of K2CO3 in acetone yielding isopropyl 2-[4-(4-isobutoxy-2-thiazolin-2-yloxy) phenyl]acetate (IV).Elimination of isobutanol from (IV) by means of p-toluenesulfonic acid in hot DMF affords isopropyl 2-[4-(2-thiazolyloxy)phenyl] acetate (V),which is methylated with methyl bromide and KOH in DMF giving isopropyl 2-[4-(2-thiazo)yloxy)phenyl]propionate (VI).Finally,this compound is hydrolyzed with NaOH in aqueous methanol.

合成路线:The condensation of 2-chlorothiazole (VII) with isopropyl 2-(4-hydroxyphenyl)propionate (VIII) by means of K2CO3 in DMF at 150 C gives (VI),previously obtained.
参考文献标题:480156-S
文献作者:Castar,J.; Serradell,M.N.; Arrigoni-Martelli,E.
参考来源:Drugs Fut 1985,10(1),37


产品链接: CAS No. 56355-17-0››