Zetidoline, DL-308
折替多林Chemical Name: 1-(3-Chlorophenyl)-3-[2-(3,3-dimethyl-1-azetidinyl)ethyl]-2-imidazolidinone
CAS No. 51940-78-4
项目整合开发状态: Biological Testing
项目研究机构: Aventis Pharma (Originator), Lepetit (Originator)
合成路线:This compound can be obtained in two different ways:1) The reduction of m-chlorophenylcarbamylmethylaminoacetic acid ethyl ester (I) with LiAlH4 in ether gives 2-(m-chlorophenylamino)ethylamino ethanol (II),which is cyclized by reaction with Cl2CO and KOH in toluene to afford 1-(m-chlorophenyl)-3-(2-hydroxyethyl)imidazolidin-2-one (III).The reaction of (III) with SOCl2 in refluxing chloroform yields 1-(m-chlorophenyl)-3-(2-chloroethyl)imidazolidin-2-one (IV),which is finally condensed with 3,3-dimethylazetidine (V) by heating at 150-60 C in benzene in a pressure vessel.2) By condensation of 1-(m-chlorophenyl)imidazolidin-2-one (VI) with 1-(2-chloroethyl)-3,3-dimethylazetidine (VII) by means of NaH in DMF at 80.5 C.
📌 参考资料/链接：
参考文献标题:2-Imidazolidione derivatives
文献作者:Fontanella,L.; Maffii,G.(Lepetit SpA)
参考来源:US 4011238
📄 详细内容
合成路线:This compound can be obtained in two different ways:1) The reduction of m-chlorophenylcarbamylmethylaminoacetic acid ethyl ester (I) with LiAlH4 in ether gives 2-(m-chlorophenylamino)ethylamino ethanol (II),which is cyclized by reaction with Cl2CO and KOH in toluene to afford 1-(m-chlorophenyl)-3-(2-hydroxyethyl)imidazolidin-2-one (III).The reaction of (III) with SOCl2 in refluxing chloroform yields 1-(m-chlorophenyl)-3-(2-chloroethyl)imidazolidin-2-one (IV),which is finally condensed with 3,3-dimethylazetidine (V) by heating at 150-60 C in benzene in a pressure vessel.2) By condensation of 1-(m-chlorophenyl)imidazolidin-2-one (VI) with 1-(2-chloroethyl)-3,3-dimethylazetidine (VII) by means of NaH in DMF at 80.5 C.
参考文献标题:Zetidoline
文献作者:Blancafort,P.; Serradell,M.N.; Castar,J.; McGillion,F.B.
参考来源:Drugs Fut 1981,6(3),162
产品链接: CAS No. 51940-78-4››