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【结 构 式】

【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%

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:(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
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