Docarpamine, TA-870, TA-8704, Tanadopa
朵卡派明Chemical Name: N-(N-Acetyl-L-methionyl)-O,O-bis(ethoxycarbonyl)dopamine; (-)-(S)-2-Acetamido-N-(3,4-dihydroxyphenethyl)-4-(methylsulfanyl)butyramide bis(ethylcarbonate) ester; N-(N-Acetyl-L-methionyl)-3,4-di(ethoxycarbonyloxy)phenethylamine
CAS No. 74639-40-0
项目整合开发状态: Launched-1994
项目研究机构: Tanabe Seiyaku (Originator), Novartis (Licensee)
合成路线:This compound can be obtained in three similar ways:1) The reaction of N-acetyl-L-methionine (I) with ethyl chloroformate (II) and triethylamine in chloroform gives the corresponding mixed anhydride (III),which is then condensed with 3,4-di(ethoxycarbonyloxy)phenethylamine tosylate (IV) by means of triethylamine in chloroform.2) The reaction of N-acetyl-L-methionine (I) with N-hydroxysuccinimide (V) by means of dicyclohexylcarbodiimide (DDC) in dioxane gives the corresponding active ester (VI),which is then condensed with the amine (IV) as before.The active ester method can also be carried out in this case using N-hydroxyphthalimide,1-hydroxybenzothiazole or 4-nitrophenol instead of N-hydroxysuccinimide (V).3) The reaction of the active ester (VI) with dopamine (VII) by means of triethylamine in DMF gives the corresponding amide (VIII),which is then acylated with ethyl chloroformate (IX) in pyridine.
📌 参考资料/链接：
参考文献标题:Phenethylamine derivs.,process for preparing same and pharmaceutical compositions containing said phenethylamine derivs
文献作者:Kiguchi,T.; Hatashi,K.; Yamaguchi,I.(Tanabe Seiyaku Co.,Ltd.)
参考来源:EP 0007441; JP 1980007242
📄 详细内容
合成路线:This compound can be obtained in three similar ways:1) The reaction of N-acetyl-L-methionine (I) with ethyl chloroformate (II) and triethylamine in chloroform gives the corresponding mixed anhydride (III),which is then condensed with 3,4-di(ethoxycarbonyloxy)phenethylamine tosylate (IV) by means of triethylamine in chloroform.2) The reaction of N-acetyl-L-methionine (I) with N-hydroxysuccinimide (V) by means of dicyclohexylcarbodiimide (DDC) in dioxane gives the corresponding active ester (VI),which is then condensed with the amine (IV) as before.The active ester method can also be carried out in this case using N-hydroxyphthalimide,1-hydroxybenzothiazole or 4-nitrophenol instead of N-hydroxysuccinimide (V).3) The reaction of the active ester (VI) with dopamine (VII) by means of triethylamine in DMF gives the corresponding amide (VIII),which is then acylated with ethyl chloroformate (IX) in pyridine.
参考文献标题:DOCARPAMINE
文献作者:Prous,J.; Castar,J.
参考来源:Drugs Fut 1990,15(2),122
产品链接: CAS No. 74639-40-0››