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【结 构 式】 
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【分子编号】29042 【品名】ethyl (2S)-1-methyl-2,3-dihydro-1H-indole-2-carboxylate 【CA登记号】 |
【 分 子 式 】C12H15NO2 【 分 子 量 】205.25664 【元素组成】C 70.22% H 7.37% N 6.82% O 15.59% |
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：(I)The condensation of ethyl indoline-2-carboxylate (I) with N-benzyloxycarbonylalanine (II) by means of CH2Cl2 gives ethyl N-(benzyloxycarbonylalanyl)indoline-2-carboxylate (III), which is hydrolyzed partially with LiOH in DMF water yielding N-(benzyloxycarbonylalanyl)indoline-2-carboxylic acid (IV). Debenzylation of (IV) by hydrogenation with H2 over Pd/C in aqueous ethanol affords N-alanylindoline-2-carboxylic acid, which is finally reductocondensed with ethyl 2-oxo-3-phenylbutyrate (VI) by means of NaOH and sodium cyanoborohydride or H2 and RaNi in ethanol.
| 【1】 Renfroe, H.B.; Stanton, J.L.; Sele, A. (Novartis AG); 1-Carboxy-azaalkyl-indolin-2-carboxylic acids, process for preparing them, pharmaceutical compositions containing them and their therapeutical use. DD 201888; EP 0051301; GB 2086390 . |
| 【2】 Serradell, M.N.; Castaner, J.; CGS-13928C. Drugs Fut 1985, 10, 3, 190. |
| 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) | 29042 | ethyl (2S)-1-methyl-2,3-dihydro-1H-indole-2-carboxylate | C12H15NO2 | 详情 | 详情 | |
| (II) | 61209 | CBZ-L-Alanine; (2S)-2-[[(Benzyloxy)carbonyl]amino]propionic acid; N-((Phenylmethoxy)carbonyl)-alanine; Carbobenzyloxy-L-alanine | C11H13NO4 | 详情 | 详情 | |
| (III) | 29043 | ethyl (2S)-1-((2S)-2-[[(benzyloxy)carbonyl]amino]propanoyl)-2,3-dihydro-1H-indole-2-carboxylate | C22H24N2O5 | 详情 | 详情 | |
| (IV) | 29044 | (2S)-1-((2S)-2-[[(benzyloxy)carbonyl]amino]propanoyl)-2,3-dihydro-1H-indole-2-carboxylic acid | C20H20N2O5 | 详情 | 详情 | |
| (V) | 29045 | (2S)-1-[(2S)-2-aminopropanoyl]-2,3-dihydro-1H-indole-2-carboxylic acid | C12H14N2O3 | 详情 | 详情 | |
| (VI) | 20896 | Ethyl 2-oxo-4-phenylbutanoate; 2-Oxo-4-phenylbutyric acid ethyl ester | 64920-29-2 | C12H14O3 | 详情 | 详情 |
Extended Information