Zetidoline, DL-308-药物合成数据库

【药物名称】Zetidoline, DL-308

化学结构式(Chemical Structure):

参考文献No.	47484
标题:	2-Imidazolidione derivatives
作者:	Fontanella, L.; Maffii, G. (Lepetit SpA)
来源:	US 4011238

合成路线图解说明: 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No.	63717
标题:	Zetidoline
作者:	Blancafort, P.; Serradell, M.N.; Casta馿r, J.; McGillion, F.B.
来源:	Drugs Fut 1981,6(3),162

合成路线图解说明: 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.