sodium 2,3-dioxo-5-indolinesulfonate -Drug Synthesis Database

【结构式】

【分子编号】49816

【品名】sodium 2,3-dioxo-5-indolinesulfonate

【CA登记号】

【分子式】C₈H₄NNaO₅S

【分子量】249.179268

【元素组成】C 38.56% H 1.62% N 5.62% Na 9.23% O 32.1% S 12.87%

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：(VI)

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.

参考文献中间体

合成目标

【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

Extended Information