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【结 构 式】

【分子编号】11235

【品名】(2S)-2-(Acetamido)-N-(3,4-dihydroxyphenethyl)-4-(methylsulfanyl)butanamide

【CA登记号】122570-36-9

【 分 子 式 】C15H22N2O4S

【 分 子 量 】326.41676

【元素组成】C 55.19% H 6.79% N 8.58% O 19.61% S 9.82%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VIII)

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
Extended Information