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【结 构 式】 
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【分子编号】49818 【品名】5-[[(2S)-2-(phenoxymethyl)pyrrolidinyl]sulfonyl]-1H-indole-2,3-dione 【CA登记号】 |
【 分 子 式 】C19H18N2O5S 【 分 子 量 】386.4284 【元素组成】C 59.06% H 4.7% N 7.25% O 20.7% S 8.3% |
合成路线1
该中间体在本合成路线中的序号：(VIII)Treatment of N-Boc-prolinol (I) with p-toluenesulfonyl chloride and pyridine afforded tosylate (II), which was condensed with the sodium salt of phenol (III) to produce ether (IV). Acid cleavage of the Boc protecting group of (IV) then gave pyrrolidine (V). Sulfonyl chloride (VII) was prepared by chlorination of the sodium salt of 5-isatinsulfonic acid (VI) with POCl3 in tetramethylenesulfone. Acylation of pyrrolidine (V) with acid chloride (VII) gave sulfonamide (VIII). Finally, the isatin nitrogen atom was methylated employing iodomethane in the presence of K2CO3.
| 【1】 Lee, D.; et al.; Potent and selective nonpeptide inhibitors of caspases 3 and 7. J Med Chem 2001, 44, 12, 2015. |
| 【2】 Long, S.A.; Lee, D. (SmithKline Beecham Corp.); Caspases and apoptosis. EP 1001933; JP 2001512100; WO 9906367 . |
| 【3】 Lee, D.; Long, S.A.; Elliott, J.D.; Gleason, J.G. (SmithKline Beecham Corp.); Caspases and apoptosis. WO 0122966 . |
| 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) | 49819 | (S)-1-(tert-Butoxycarbonyl)-2-pyrrolidinenemethanol | C10H19NO3 | 详情 | 详情 | |
| (II) | 49813 | tert-butyl (2S)-2-([[(4-methylphenyl)sulfonyl]oxy]methyl)-1-pyrrolidinecarboxylate | C17H25NO5S | 详情 | 详情 | |
| (III) | 23540 | Phenol | 108-95-2 | C6H6O | 详情 | 详情 |
| (IV) | 49814 | tert-butyl (2S)-2-(phenoxymethyl)-1-pyrrolidinecarboxylate | C16H23NO3 | 详情 | 详情 | |
| (V) | 49815 | phenyl (2S)pyrrolidinylmethyl ether; (2S)-2-(phenoxymethyl)pyrrolidine | C11H15NO | 详情 | 详情 | |
| (VI) | 49816 | sodium 2,3-dioxo-5-indolinesulfonate | C8H4NNaO5S | 详情 | 详情 | |
| (VII) | 49817 | 2,3-dioxo-5-indolinesulfonyl chloride | C8H4ClNO4S | 详情 | 详情 | |
| (VIII) | 49818 | 5-[[(2S)-2-(phenoxymethyl)pyrrolidinyl]sulfonyl]-1H-indole-2,3-dione | C19H18N2O5S | 详情 | 详情 |