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【结 构 式】 
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【分子编号】26285 【品名】(2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl](methyl)amino]-3-(1H-indol-3-yl)propionic acid 【CA登记号】 |
【 分 子 式 】C27H24N2O4 【 分 子 量 】440.49864 【元素组成】C 73.62% H 5.49% N 6.36% O 14.53% |
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：(XXIV)A more effective preparation of (XXII) was further developed starting from N-methyltryptophan (XXIII). Protection as the N-Fmoc derivative (XXIV) and then esterification with (trimethylsilyl)diazomethane yielded (XXV). Reduction of (XXV) with triethylsilane and TFA produced indoline (XXVI), which was reoxidized to the corresponding N-hydroxyindole with Na2WO4 and H2O2, and then O-methylated with Me2SO4 to give (XXVII). Finally, Fmoc deprotection of (XXVII) with Et2NH provided aminoester (XXII).
| 【1】 Boger, D.L.; et al.; Total synthesis of HUN-7293. J Am Chem Soc 1999, 121, 26, 6197. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 40597 | 9-[[(chlorocarbonyl)oxy]methyl]-9H-fluorene | 28920-43-6 | C15H11ClO2 | 详情 | 详情 | |
| (XXII) | 26283 | methyl (2S)-3-(1-methoxy-1H-indol-3-yl)-2-(methylamino)propanoate | C14H18N2O3 | 详情 | 详情 | |
| (XXIII) | 26284 | N-alpha-Methyl-L-tryptophan; L-Abrine; (2S)-3-(1H-Indol-3-yl)-2-(methylamino)propionic acid; N-Methyl-L-tryptophan | 526-31-8 | C12H14N2O2 | 详情 | 详情 |
| (XXIV) | 26285 | (2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl](methyl)amino]-3-(1H-indol-3-yl)propionic acid | C27H24N2O4 | 详情 | 详情 | |
| (XXV) | 26286 | methyl (2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl](methyl)amino]-3-(1H-indol-3-yl)propanoate | C28H26N2O4 | 详情 | 详情 | |
| (XXVI) | 26287 | methyl (2S)-3-(2,3-dihydro-1H-indol-3-yl)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl](methyl)amino]propanoate | C28H28N2O4 | 详情 | 详情 | |
| (XXVII) | 26288 | methyl (2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl](methyl)amino]-3-(1-methoxy-1H-indol-3-yl)propanoate | C29H28N2O5 | 详情 | 详情 |
Extended Information