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【结 构 式】 
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【分子编号】47085 【品名】3-(2-sulfanylbenzoyl)-1,3-thiazolidine-2-carboxylic acid 【CA登记号】 |
【 分 子 式 】C11H11NO3S2 【 分 子 量 】269.34528 【元素组成】C 49.05% H 4.12% N 5.2% O 17.82% S 23.81% |
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 2,2'-dithiobis(benzoic acid) (I) with thionyl chloride produced the corresponding acid chloride (II), which was further condensed with thiazolidine-2-carboxylic acid (III) in the presence of Na2CO3 to furnish diamide (IV). Reductive cleavage of the disulfide group of (IV) by means of NaBH4 in refluxing EtOH yielded thiol (V). Finally, intramolecular cyclization of (V) to give the title tricyclic compound was achieved by treatment with carbonyl diimidazole in boiling THF.
| 【1】 Neamati, N.; Winslow, H.E.; Turpin, J.A.; et al.; Thiazolothiazepine inhibitors of HIV-1 integrase. J Med Chem 1999, 42, 17, 3334. |
| 【2】 Garofalo, A.; Pommier, Y.; Neamati, N.; Nacci, V. (US Department of Health & Human Services); Thiazepine inhibitors of HIV-1 integrase. WO 0068235 . |
| 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) | 20404 | 2-[(2-carboxyphenyl)disulfanyl]benzoic acid; 2,2'-Dithiodibenzoic acid | 119-80-2 | C14H10O4S2 | 详情 | 详情 |
| (II) | 20405 | 2-[[2-(chlorocarbonyl)phenyl]disulfanyl]benzoyl chloride | C14H8Cl2O2S2 | 详情 | 详情 | |
| (III) | 47083 | 1,3-thiazolidine-2-carboxylic acid | C4H7NO2S | 详情 | 详情 | |
| (IV) | 47084 | 3-[2-([2-[(2-carboxy-1,3-thiazolidin-3-yl)carbonyl]phenyl]disulfanyl)benzoyl]-1,3-thiazolidine-2-carboxylic acid | C22H20N2O6S4 | 详情 | 详情 | |
| (V) | 47085 | 3-(2-sulfanylbenzoyl)-1,3-thiazolidine-2-carboxylic acid | C11H11NO3S2 | 详情 | 详情 |
Extended Information