• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】36431

【品名】diethyl 2-aminononanedioate

【CA登记号】

【 分 子 式 】C13H25NO4

【 分 子 量 】259.34584

【元素组成】C 60.21% H 9.72% N 5.4% O 24.68%

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:(V)

The condensation of diethyl acetamidomalonate (I) with ethyl 7-bromoheptanoate (II) by means of sodium ethoxide in refluxing ethanol gives diethyl acetamido-(6-ethoxycarbonylhexyl)malonate (III), which is hydrolyzed and decarboxylated with refluxing concentrated HCl yielding 2-aminononanedioic acid (IV). This acid is esterified with SOCl2 and ethanol to the corresponding diethyl ester (V), which is condensed with vinyl cyclohexyl ketone (VI) to afford diethyl 2-[(3-oxo-3-cyclohexylpropyl)amino]nonanedioate (VII). The reaction of (VII) with potassium cyanate in ethanol-HCl gives the corresponding hydantoic ester (VIII), which is cyclized by heating at 100 C affording 5-(6-carboxyhexyl)-1-(3-cyclohexyl-3-oxopropyl)hydantoin (IX). Finally, this compound is reduced with NaBH4 in ethanol.

1 Whittaker, N.; Harris, C.J.; Stepney, R.; Caldwell, A.G.; Heterocyclic prostaglandin analogs. Part 2. Hydantoins and other imidazole analogs. J Chem Soc - Perkins Trans I 1980, 1, 2, 495-505.
2 Harris, C.J.; Stepney, R.; Caldwell, A.G.; Whittaker, N.; Hydantoin prostaglandin analog, potemt and selective inhibitors of platelet aggregation. J Chem Soc Chem Commun 1979, 13, 561-562.
3 Caldwell, A.G.; Whittaker, N.; US 4204068 .
4 Caldwell, A.G.; Whittaker, N.; BE 0876670 .
5 Serradell, M.N.; Blancafort, P.; Castaner, J.; Hillier, K.; BW-245-C. Drugs Fut 1982, 7, 6, 380.
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) 16710 Diethyl 2-(acetamido)malonate; Diethyl acetamidomalonate 1068-90-2 C9H15NO5 详情 详情
(II) 36428 ethyl 7-bromoheptanoate 29823-18-5 C9H17BrO2 详情 详情
(III) 36429 triethyl 1-(acetamido)-1,1,7-heptanetricarboxylate C18H31NO7 详情 详情
(IV) 36430 2-aminononanedioic acid C9H17NO4 详情 详情
(V) 36431 diethyl 2-aminononanedioate C13H25NO4 详情 详情
(VI) 36432 1-cyclohexyl-2-propen-1-one C9H14O 详情 详情
(VII) 36433 diethyl 2-[(3-cyclohexyl-3-oxopropyl)amino]nonanedioate C22H39NO5 详情 详情
(VIII) 36434 diethyl 2-[(aminocarbonyl)(3-cyclohexyl-3-oxopropyl)amino]nonanedioate C23H40N2O6 详情 详情
(IX) 36435 7-[3-(3-cyclohexyl-3-oxopropyl)-2,5-dioxo-4-imidazolidinyl]heptanoic acid C19H30N2O5 详情 详情
Extended Information