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【结 构 式】 
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【分子编号】64520 【品名】benzyl (3S)-2,6-dioxopiperidinylcarbamate 【CA登记号】 |
【 分 子 式 】C13H14N2O4 【 分 子 量 】262.26524 【元素组成】C 59.54% H 5.38% N 10.68% O 24.4% |
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)The cyclization of N-(benzyloxycarbonyl)-L-glutamine (I) by means of CDI in THF gives the piperidinedione (II), which is deprotected by means of HBr in AcOH to yield 3(S)-aminopiperidine-2,6-dione (III).The condensation of (III) with 3-nitrophthalic anhydride (IV) in hot DMF/AcOH affords 3(S)-phthalimido-piperidine-2,6-dione (V), which is finally reduced with H2 over Pd/C in dioxane/methanol to provide the target thalidomide derivative.
| 【1】 D'Amato, R.J.; Shah, J.H.; Hunsucker, K.A.; Pribluda, V.; Treston, A.; Rougas, J.; Conner, B.P.; Swartz, G.M. (Children's Medical Center Corp.); Synthesis of 3-amino-thalidomide and its enantiomers. WO 0264083 . |
| 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) | 26289 | (2S)-5-amino-2-[[(benzyloxy)carbonyl]amino]-5-oxopentanoic acid | C13H16N2O5 | 详情 | 详情 | |
| (II) | 64520 | benzyl (3S)-2,6-dioxopiperidinylcarbamate | C13H14N2O4 | 详情 | 详情 | |
| (III) | 48171 | (3S)-3-amino-2,6-piperidinedione | C5H8N2O2 | 详情 | 详情 | |
| (IV) | 46407 | 4-nitro-2-benzofuran-1,3-dione；3-nitrophthalic anhydride | 641-70-3 | C8H3NO5 | 详情 | 详情 |
| (V) | 34429 | 2-[(3S)-2,6-dioxopiperidinyl]-4-nitro-1H-isoindole-1,3(2H)-dione | C13H9N3O6 | 详情 | 详情 |
Extended Information