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【结 构 式】 
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【分子编号】34428 【品名】(2S)-5-amino-2-(4-nitro-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-5-oxopentanoic acid 【CA登记号】 |
【 分 子 式 】C13H11N3O7 【 分 子 量 】321.24636 【元素组成】C 48.61% H 3.45% N 13.08% O 34.86% |
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)Treatment of 3-nitrophthalimide (I) with ethyl chloroformate and triethylamine produced 3-nitro-N-(ethoxycarbonyl)phthalimide (II), which was condensed with L-glutamine tert-butyl ester hydrochloride (III) to afford the phthaloyl glutamine derivative (IV). Acidic cleavage of the tert-butyl ester of (IV) provided the corresponding carboxylic acid (V). This was cyclized to the required glutarimide (VI) upon treatment with thionyl chloride and then with triethylamine. The nitro group of (VI) was finally reduced to amine by hydrogenation over Pd/C.
| 【1】 Muller, G.W.; Huang, S.-Y.; Chen, R.; et al.; Amino-substituted thalidomide analogs: Potent inhibitors of TNF-alpha production. Bioorg Med Chem Lett 1999, 9, 11, 1625. |
| 【2】 Stirling, D.I.; Chen, R.S.-C.; Muller, G.W. (Celgene Corp.); Substd. 2-(2,6-dioxopiperidin-3-yl)-phthalimides and 1-oxoisoindolines and method of reducing TNFalpha levels. EP 0925294; EP 0984955; US 5635517; WO 9803502; WO 9854170 . |
| 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) | 34424 | 4-nitro-1H-isoindole-1,3(2H)-dione；3-nitrophthalimide | 603-62-3 | C8H4N2O4 | 详情 | 详情 |
| (II) | 34425 | ethyl 4-nitro-1,3-dioxo-1,3-dihydro-2H-isoindole-2-carboxylate | C11H8N2O6 | 详情 | 详情 | |
| (III) | 34426 | tert-butyl (2S)-2,5-diamino-5-oxopentanoate | C9H18N2O3 | 详情 | 详情 | |
| (IV) | 34427 | tert-butyl (2S)-5-amino-2-(4-nitro-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-5-oxopentanoate | C17H19N3O7 | 详情 | 详情 | |
| (V) | 34428 | (2S)-5-amino-2-(4-nitro-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-5-oxopentanoic acid | C13H11N3O7 | 详情 | 详情 | |
| (VI) | 34429 | 2-[(3S)-2,6-dioxopiperidinyl]-4-nitro-1H-isoindole-1,3(2H)-dione | C13H9N3O6 | 详情 | 详情 |
Extended Information