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【结 构 式】

【分子编号】26284

【品名】N-alpha-Methyl-L-tryptophan; L-Abrine; (2S)-3-(1H-Indol-3-yl)-2-(methylamino)propionic acid; N-Methyl-L-tryptophan

【CA登记号】526-31-8

【 分 子 式 】C12H14N2O2

【 分 子 量 】218.25544

【元素组成】C 66.04% H 6.47% N 12.84% O 14.66%

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:(XXIII)

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