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【结 构 式】 
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【分子编号】40966 【品名】2-chloro-3-(2-chloroethyl)-1,3,2lambda(5)-oxazaphosphinan-2-one 【CA登记号】 |
【 分 子 式 】C5H10Cl2NO2P 【 分 子 量 】218.019102 【元素组成】C 27.55% H 4.62% Cl 32.52% N 6.42% O 14.68% P 14.21% |
合成路线1
该中间体在本合成路线中的序号：(I)By alkylation of 2-chloro-3-(2-chloroethyl)perhydro-1,3,2-oxaazaphosphorine (I) with 2-chloroethylamine (II) by means of TEA in dichloromethane.
| 【1】 Arnold, H.; et al. (Asta Medica AG); Verfahren zur Herstellung von neuen N-substituierten Amiden und Esteramiden der Phosphosaure und Thiophosphosaure. DE 1645921 . |
合成路线2
该中间体在本合成路线中的序号：(I)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 |