【结 构 式】 |
【药物名称】Ipenoxazone, MLV-6976, NC-1200 【化学名称】(+)-(4S,5R)-4-(2-Methylpropyl)-3-[3-(perhydroazepin-1-yl)propyl]-5-phenyl-1,3-oxazolidin-2-one 【CA登记号】104454-71-9 【 分 子 式 】C22H34N2O2 【 分 子 量 】358.52848 |
【开发单位】Nippon Chemiphar (Originator) 【药理作用】Alzheimer's Dementia, Treatment of , Cognition Disorders, Treatment of, NEUROLOGIC DRUGS, Neurologic Drugs (Miscellaneous), Glutamate Ionotropic Antagonists |
合成路线1
Protected aminopentanoic acid derivative (I) is converted into phenylpentanone (II) by first treatment with thionyl chloride in refluxing benzene, followed by condensation with benzene and aluminum chloride. Reduction of (II) with aluminum isopropoxide in refluxing isopropanol provides phenylpentanol derivative (III), which is then treated with hydrazine hydrate in refluxing EtOH to furnish 2-amino-4-methyl-1-phenylpentane-1-ol (IV). Coupling of (IV) with chloro derivative (V) at 110-120 C yields derivative (VI), which is finally converted into the desired oxazolidinone by reaction with ethyl chlorocarbonate (VII) in chloroform followed by heating in toluene and treatment with aluminum isopropoxide.
【1】 Moritoh, N.; Satoh, M.; Shinozaki, H.; Masaki, M.; Hashimoto, K.; Kamishiro, T. (Nippon Chemiphar Co., Ltd.); 1,3-Oxazolidin-2-one derivs.. CH 663207; DE 3519261; ES 8800571; ES 8802152; FR 2571052; GB 2165237; JP 1986083170; US 4644063 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
13364 | Benzene | 71-43-2 | C6H6 | 详情 | 详情 | |
(I) | 50833 | (2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-methylpentanoic acid | C14H15NO4 | 详情 | 详情 | |
(II) | 50834 | 2-[(1S)-1-benzoyl-3-methylbutyl]-1H-isoindole-1,3(2H)-dione | C20H19NO3 | 详情 | 详情 | |
(III) | 50835 | 2-[(1S)-1-[(R)-hydroxy(phenyl)methyl]-3-methylbutyl]-1H-isoindole-1,3(2H)-dione | C20H21NO3 | 详情 | 详情 | |
(IV) | 50836 | (1R,2S)-2-amino-4-methyl-1-phenyl-1-pentanol | C12H19NO | 详情 | 详情 | |
(V) | 50837 | 1-(3-chloropropyl)azepane | C9H18ClN | 详情 | 详情 | |
(VI) | 50838 | (1R,2S)-2-[[3-(1-azepanyl)propyl]amino]-4-methyl-1-phenyl-1-pentanol | C21H36N2O | 详情 | 详情 | |
(VII) | 11229 | 1-[(Chlorocarbonyl)oxy]ethane;ethyl carbonochloridate; Carbonchloridic acid ethyl ester;Ethyl chloroformate;Ethyl chlorocarbonate | 541-41-3 | C3H5ClO2 | 详情 | 详情 |