【结 构 式】 |
【分子编号】11231 【品名】4-(2-aminoethyl)-2-[(ethoxycarbonyl)oxy]phenyl ethyl carbonate 【CA登记号】 |
【 分 子 式 】C14H19NO6 【 分 子 量 】297.308 【元素组成】C 56.56% H 6.44% N 4.71% O 32.29% |
合成路线1
该中间体在本合成路线中的序号:(IV)This compound can be obtained in three similar ways: 1) The reaction of N-acetyl-L-methionine (I) with ethyl chloroformate (II) and triethylamine in chloroform gives the corresponding mixed anhydride (III), which is then condensed with 3,4-di(ethoxycarbonyloxy)phenethylamine tosylate (IV) by means of triethylamine in chloroform. 2) The reaction of N-acetyl-L-methionine (I) with N-hydroxysuccinimide (V) by means of dicyclohexylcarbodiimide (DDC) in dioxane gives the corresponding active ester (VI), which is then condensed with the amine (IV) as before. The active ester method can also be carried out in this case using N-hydroxyphthalimide, 1-hydroxybenzothiazole or 4-nitrophenol instead of N-hydroxysuccinimide (V). 3) The reaction of the active ester (VI) with dopamine (VII) by means of triethylamine in DMF gives the corresponding amide (VIII), which is then acylated with ethyl chloroformate (IX) in pyridine.
【1】 Kiguchi, T.; Hatashi, K.; Yamaguchi, I. (Tanabe Seiyaku Co., Ltd.); Phenethylamine derivs., process for preparing same and pharmaceutical compositions containing said phenethylamine derivs. EP 0007441; JP 1980007242 . |
【2】 Prous, J.; Castaner, J.; DOCARPAMINE. Drugs Fut 1990, 15, 2, 122. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
60593 | p-xylene | C8H10 | 详情 | 详情 | ||
(II), (IX) | 11229 | 1-[(Chlorocarbonyl)oxy]ethane;ethyl carbonochloridate; Carbonchloridic acid ethyl ester;Ethyl chloroformate;Ethyl chlorocarbonate | 541-41-3 | C3H5ClO2 | 详情 | 详情 |
(I) | 11228 | (2S)-2-(Acetamido)-4-(methylsulfanyl)butyric acid | 65-82-7 | C7H13NO3S | 详情 | 详情 |
(III) | 11230 | N-Acetyl-L-methionine ethoxycarbonyl anhydride | C10H17NO5S | 详情 | 详情 | |
(IV) | 11231 | 4-(2-aminoethyl)-2-[(ethoxycarbonyl)oxy]phenyl ethyl carbonate | C14H19NO6 | 详情 | 详情 | |
(V) | 10264 | 1-Hydroxydihydro-1H-pyrrole-2,5-dione; N-Hydroxysuccinimide; 1-Hydroxy-2,5-pyrrolidinedione | 6066-82-6 | C4H5NO3 | 详情 | 详情 |
(VI) | 11233 | N-[(1S)-1-[[(2,5-Dioxo-1-pyrrolidinyl)oxy]carbonyl]-3-(methylsulfanyl)propyl]acetamide | C11H16N2O5S | 详情 | 详情 | |
(VII) | 11234 | 4-(2-Aminoethyl)-1,2-benzenediol | 51-61-6 | C8H11NO2 | 详情 | 详情 |
(VIII) | 11235 | (2S)-2-(Acetamido)-N-(3,4-dihydroxyphenethyl)-4-(methylsulfanyl)butanamide | 122570-36-9 | C15H22N2O4S | 详情 | 详情 |