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【结 构 式】

【药物名称】Sufosfamide, 036.5122, Asta 5122

【化学名称】2-[3-(2-Chloroethyl)-2-oxidotetrahydro-2H-1,3,2-oxazaphosphorin-2-ylamino]ethyl methanesulfonate

【CA登记号】37753-10-9

【 分 子 式 】C8H18ClN2O5PS

【 分 子 量 】320.73386

【开发单位】

【药理作用】 

合成路线1

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)

1 (Asta-Werke A.G.); FR 2125595 .
2 Arnold, H.; et al. (Asta-Werke A.G.); DE 2107936 .
3 Castaner, J.; Hillier, K.; Sufosfamide. Drugs Fut 1977, 2, 5, 339.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 40966 2-chloro-3-(2-chloroethyl)-1,3,2lambda(5)-oxazaphosphinan-2-one C5H10Cl2NO2P 详情 详情
(II) 10259 Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol;2-Aminoethyl alcohol 141-43-5 C2H7NO 详情 详情
(III) 60926 3-(2-chloroethyl)-2-[(2-hydroxyethyl)amino]-1,3,2lambda~5~-oxazaphosphinan-2-one C7H16ClN2O3P 详情 详情
(IV) 60931 2-aminoethyl methanesulfonate C3H9NO3S 详情 详情
(V) 33455 2-chloro-1-ethanamine; 2-chloroethylamine C2H6ClN 详情 详情
(VI) 60927 3-(2-chloroethyl)-2-[(2-chloroethyl)amino]-1,3,2lambda~5~-oxazaphosphinan-2-one C7H15Cl2N2O2P 详情 详情
(VII) 60930 3-[(2-chloroethyl)amino]-1-propanol C5H12ClNO 详情 详情
(VIII) 60929 2-[(dichlorophosphoryl)amino]ethyl methanesulfonate C3H8Cl2NO4PS 详情 详情
(IX) 60928 2-(1-aziridinyl)-3-(2-chloroethyl)-1,3,2lambda~5~-oxazaphosphinan-2-one C7H14ClN2O2P 详情 详情
Extended Information