N-alpha-Methyl-L-tryptophan; L-Abrine; (2S)-3-(1H-Indol-3-yl)-2-(methylamino)propionic acid; N-Methyl-L-tryptophan -Drug Synthesis Database

【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).

参考文献中间体

合成目标

【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