Sufosfamide, 036.5122, Asta 5122
Chemical Name: 2-[3-(2-Chloroethyl)-2-oxidotetrahydro-2H-1,3,2-oxazaphosphorin-2-ylamino]ethyl methanesulfonate
项目整合开发状态: Biological Testing
项目研究机构:
合成路线:It can be prepared in several different ways:1) By condensation of (I) with ethanolamine (II) by means of triethylamine in dioxane that gives 2-(2-hydroxyethylamino)-3-(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide (III),which is then esterified with methanesulfonyl chloride and triethylamine in dioxane.(1,2)2) By condensation of 2-chloro-3-(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide (I) with 2-(methylsulfonyloxy)ethylamine by means of triethylamine (IV) in CH2Cl2.(1,2)3) By condensation of (I) with 2-chloroethylamine (V) by means of triethylamine in CH2Cl2 that gives 2-(2-chloroethylamino)-3-(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide (VI),which is then transformed into the ester by means of silver methanesulfonate in refluxing acetonitrile.(1,2)4) By cyclization at N-(3-hydroxypropyl)-2-chloroethylamine (VII) with N-(2-methylsulfonyl-oxyethyl)dichlorophosphoramide (VIII) by means of triethylamine in CH2Cl2.(1,2)5) By mesylation of 2-(ethyleneimino)-3-(2-chloroethyl)tetrahydro-2H-1,3,2-oxaza-phosphorine-2-oxide (IX) with methanesulfonic acid in ethyl ether.(1,2)
📌 参考资料/链接：
参考文献标题:Sufosfamide
文献作者:Casta馿r,J.; Hillier,K.
参考来源:Drugs Fut 1977,2(5),339
📄 详细内容
合成路线:It can be prepared in several different ways:1) By condensation of (I) with ethanolamine (II) by means of triethylamine in dioxane that gives 2-(2-hydroxyethylamino)-3-(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide (III),which is then esterified with methanesulfonyl chloride and triethylamine in dioxane.(1,2)2) By condensation of 2-chloro-3-(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide (I) with 2-(methylsulfonyloxy)ethylamine by means of triethylamine (IV) in CH2Cl2.(1,2)3) By condensation of (I) with 2-chloroethylamine (V) by means of triethylamine in CH2Cl2 that gives 2-(2-chloroethylamino)-3-(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide (VI),which is then transformed into the ester by means of silver methanesulfonate in refluxing acetonitrile.(1,2)4) By cyclization at N-(3-hydroxypropyl)-2-chloroethylamine (VII) with N-(2-methylsulfonyl-oxyethyl)dichlorophosphoramide (VIII) by means of triethylamine in CH2Cl2.(1,2)5) By mesylation of 2-(ethyleneimino)-3-(2-chloroethyl)tetrahydro-2H-1,3,2-oxaza-phosphorine-2-oxide (IX) with methanesulfonic acid in ethyl ether.(1,2)
参考文献标题:
文献作者:Arnold,H.; et al.(Asta-Werke A.G.)
参考来源:DE 2107936
合成路线:It can be prepared in several different ways:1) By condensation of (I) with ethanolamine (II) by means of triethylamine in dioxane that gives 2-(2-hydroxyethylamino)-3-(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide (III),which is then esterified with methanesulfonyl chloride and triethylamine in dioxane.(1,2)2) By condensation of 2-chloro-3-(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide (I) with 2-(methylsulfonyloxy)ethylamine by means of triethylamine (IV) in CH2Cl2.(1,2)3) By condensation of (I) with 2-chloroethylamine (V) by means of triethylamine in CH2Cl2 that gives 2-(2-chloroethylamino)-3-(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide (VI),which is then transformed into the ester by means of silver methanesulfonate in refluxing acetonitrile.(1,2)4) By cyclization at N-(3-hydroxypropyl)-2-chloroethylamine (VII) with N-(2-methylsulfonyl-oxyethyl)dichlorophosphoramide (VIII) by means of triethylamine in CH2Cl2.(1,2)5) By mesylation of 2-(ethyleneimino)-3-(2-chloroethyl)tetrahydro-2H-1,3,2-oxaza-phosphorine-2-oxide (IX) with methanesulfonic acid in ethyl ether.(1,2)
参考文献标题:
文献作者:(Asta-Werke A.G.)
参考来源:FR 2125595