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【结 构 式】

【分子编号】50834

【品名】2-[(1S)-1-benzoyl-3-methylbutyl]-1H-isoindole-1,3(2H)-dione

【CA登记号】

【 分 子 式 】C20H19NO3

【 分 子 量 】321.3758

【元素组成】C 74.75% H 5.96% N 4.36% O 14.94%

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:(II)

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
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