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【结 构 式】 
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【分子编号】42181 【品名】tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-4-[[2-(ethanimidoylamino)ethyl]sulfanyl]butanoate 【CA登记号】 |
【 分 子 式 】C17H33N3O4S 【 分 子 量 】375.53284 【元素组成】C 54.37% H 8.86% N 11.19% O 17.04% S 8.54% |
合成路线1
该中间体在本合成路线中的序号：(XIV)In a further procedure, N-Boc-L-homocysteine tert-butyl ester (XI) was prepared by reduction of N-Boc-homocystine tert-butyl ester (X) with dithiothreitol (DTT). Alkylation of thiol (XI) with tosylate (II) afforded thioether (XII). An alternative synthetic access to (XII) consisted in the esterification of carboxylic acid (VI), prepared as above, by means of either N,N-dimethylformamide di-O-t-butyl acetal or O-t-butyl 1,1,1-trichloroacetimidate. Transfer hydrogenolysis of (XII) using ammonium formate and palladium hydroxide on carbon removed the benzyloxycarbonyl group to furnish (XIII). This was converted to amidine (XIV) by treatment with S-(1-naphthylmethyl)thioacetimidate hydrochloride (VIII). Finally, deprotection of the Boc group and the tert-butyl ester of (XIV) by means of HCl in dioxan afforded the title compound.
| 【1】 Young, R.J.; et al.; Inhibition of inducible nitric oxide synthase by acetamidine derivatives of hetero-substituted lysine and homolysine. Bioorg Med Chem Lett 2000, 10, 6, 597. |
| 【2】 Beams, R.M.; Frend, A.J.; Drysdale, M.J.; Franzman, K.W.; Hodson, H.F.; Rees, D.D.; Knowles, R.G.; Sawyer, D.A. (Glaxo Wellcome plc); Nitric oxide synthase inhibitors. EP 0958277; JP 2000504041; WO 9830537 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (II) | 42170 | 2-[[(benzyloxy)carbonyl]amino]ethyl 4-methylbenzenesulfonate | C17H19NO5S | 详情 | 详情 | |
| (VI) | 42173 | (2S)-4-[(2-[[(benzyloxy)carbonyl]amino]ethyl)sulfanyl]-2-[(tert-butoxycarbonyl)amino]butyric acid | C19H28N2O6S | 详情 | 详情 | |
| (VIII) | 42175 | 1-naphthylmethyl ethanimidothioate | C13H13NS | 详情 | 详情 | |
| (X) | 42177 | di(tert-butyl) (6S,13S)-2,2,17,17-tetramethyl-4,15-dioxo-3,16-dioxa-9,10-dithia-5,14-diazaoctadecane-6,13-dicarboxylate | C26H48N2O8S2 | 详情 | 详情 | |
| (XI) | 42178 | tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-4-sulfanylbutanoate | C13H25NO4S | 详情 | 详情 | |
| (XII) | 42179 | tert-butyl (2S)-4-[(2-[[(benzyloxy)carbonyl]amino]ethyl)sulfanyl]-2-[(tert-butoxycarbonyl)amino]butanoate | C23H36N2O6S | 详情 | 详情 | |
| (XIII) | 42180 | tert-butyl (2S)-4-[(2-aminoethyl)sulfanyl]-2-[(tert-butoxycarbonyl)amino]butanoate | C15H30N2O4S | 详情 | 详情 | |
| (XIV) | 42181 | tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-4-[[2-(ethanimidoylamino)ethyl]sulfanyl]butanoate | C17H33N3O4S | 详情 | 详情 |