• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】45342

【品名】methyl (2R)-2-amino-3-(1H-indol-3-yl)-2-methylpropanoate

【CA登记号】

【 分 子 式 】C13H16N2O2

【 分 子 量 】232.28232

【元素组成】C 67.22% H 6.94% N 12.06% O 13.78%

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:(VIII)

Treatment of N(alpha)-Cbz-D-tryptophan (I) with diazomethane (CH2N2) in Et2O/CH2Cl2 provides methyl ester derivative (II), which is then cyclized to afford pyrrolo-indole derivative (III) by long treatment with TFA. N-protection of (III) by reaction with benzyl chloroformate (IV) and Na2CO3 in dioxane yields derivative (V), which is then converted into labeled methylated derivative (VI) by first deprotonation with LHDMS followed by treatment with labeled methyl iodide (MeI) in THF. Ring opening of (VI) by means of TFA furnishes protected methyltryptophan (VII), whose Cbz groups are removed by hydrogenolysis over Pd/C in EtOH to yield derivative (VIII). Coupling of (VIII) with carbonate (IX) by means of DMAP in DMF affords derivative (X), which is then subjected to saponification with LiOH in MeOH to provide carboxylic acid derivative (XI). Finally, (XI) is coupled with methylbenzylamine (XII) by means of HOBt, EDC and N-methylmorpholine (NMM).

1 Ekhato, I.V.; Huang, Y.; Tetrahydro-pyrrolo-[2,3-b]indole-1,2,8-tricarboxylic acid ester in the enantiospecific preparation of alpha-methyltryptophan: Application in the preparation of carbon-14 labeled PD 145942 and PD 154075. J Label Compd Radiopharm 1997, 39, 12, 1019.
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) 44180 (2R)-2-[[(benzyloxy)carbonyl]amino]-3-(1H-indol-3-yl)propionic acid C19H18N2O4 详情 详情
(II) 44174 methyl (2R)-2-[[(benzyloxy)carbonyl]amino]-3-(1H-indol-3-yl)propanoate C20H20N2O4 详情 详情
(III) 44175 1-benzyl 2-methyl (2R,3aS,8aS)-3,3a,8,8a-tetrahydropyrrolo[2,3-b]indole-1,2(2H)-dicarboxylate C20H20N2O4 详情 详情
(IV) 10101 Benzyloxycarbonyl chloride; Benzyl chloroformate; 1-[[(Chlorocarbonyl)oxy]methyl]benzene 501-53-1 C8H7ClO2 详情 详情
(V) 44176 1,8-dibenzyl 2-methyl (2R,3aS,8aR)-2,3,3a,8a-tetrahydropyrrolo[2,3-b]indole-1,2,8-tricarboxylate C28H26N2O6 详情 详情
(VI) 44177 1,8-dibenzyl 2-methyl (2R,3aS,8aS)-2-methyl-2,3,3a,8a-tetrahydropyrrolo[2,3-b]indole-1,2,8-tricarboxylate C29H28N2O6 详情 详情
(VI) 45341 1,8-dibenzyl 2-methyl (2R,3aS,8aS)-2-methyl-2,3,3a,8a-tetrahydropyrrolo[2,3-b]indole-1,2,8-tricarboxylate C29H28N2O6 详情 详情
(VII) 44178 benzyl 3-((2R)-2-[[(benzyloxy)carbonyl]amino]-3-methoxy-2-methyl-3-oxopropyl)-1H-indole-1-carboxylate C29H28N2O6 详情 详情
(VII) 45340 benzyl 3-((2R)-2-[[(benzyloxy)carbonyl]amino]-3-methoxy-2-methyl-3-oxopropyl)-1H-indole-1-carboxylate C29H28N2O6 详情 详情
(VIII) 44166 methyl (2R)-2-amino-3-(1H-indol-3-yl)-2-methylpropanoate C13H16N2O2 详情 详情
(VIII) 45342 methyl (2R)-2-amino-3-(1H-indol-3-yl)-2-methylpropanoate C13H16N2O2 详情 详情
(IX) 44171 1-benzofuran-2-ylmethyl 4-nitrophenyl carbonate C16H11NO6 详情 详情
(X) 44179 methyl (2R)-2-[[(1-benzofuran-2-ylmethoxy)carbonyl]amino]-3-(1H-indol-3-yl)-2-methylpropanoate C23H22N2O5 详情 详情
(X) 45343 methyl (2R)-2-[[(1-benzofuran-2-ylmethoxy)carbonyl]amino]-3-(1H-indol-3-yl)-2-methylpropanoate C23H22N2O5 详情 详情
(XI) 44173 (2R)-2-[[(1-benzofuran-2-ylmethoxy)carbonyl]amino]-3-(1H-indol-3-yl)-2-methylpropionic acid C22H20N2O5 详情 详情
(XI) 45344 (2R)-2-[[(1-benzofuran-2-ylmethoxy)carbonyl]amino]-3-(1H-indol-3-yl)-2-methylpropionic acid C22H20N2O5 详情 详情
(XII) 20042 (1S)-1-phenyl-1-ethanamine; (1S)-1-phenylethylamine C8H11N 详情 详情
Extended Information