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【结 构 式】 
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【分子编号】36435 【品名】7-[3-(3-cyclohexyl-3-oxopropyl)-2,5-dioxo-4-imidazolidinyl]heptanoic acid 【CA登记号】 |
【 分 子 式 】C19H30N2O5 【 分 子 量 】366.45768 【元素组成】C 62.27% H 8.25% N 7.64% O 21.83% |
合成路线1
该中间体在本合成路线中的序号：(IX)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 |