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【结 构 式】 
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【分子编号】30836 【品名】L-tryptophan 【CA登记号】73-22-3 |
【 分 子 式 】C11H12N2O2 【 分 子 量 】204.22856 【元素组成】C 64.69% H 5.92% N 13.72% O 15.67% |
与该中间体有关的原料药合成路线共 2 条
合成路线1
该中间体在本合成路线中的序号：(I)By acylation of L-tryptophan (I) with 4-chlorobenzoyl chloride (II).
| 【1】 Rovati, L.S.; Picciola, G.; Makovec, F. (Rotta Research Laboratorium SpA); N-p-Chlorobenzoyl tryptophane salts and compsns. thereof. US 4000297 . |
| 【2】 Blancafort, P.; Castaner, J.; Serradell, M.N.; de Angelis, L.; Benzotript. Drugs Fut 1983, 8, 6, 487. |
合成路线2
该中间体在本合成路线中的序号：(I)Esterification of L-tryptophan (I) by means of MeOH and SOCl2 gave the corresponding methyl ester (II). Subsequent Pictet-Spengler cyclization of (II) with 4-chlorobenzaldehyde (III) furnished the tetrahydropyridoindole (IV), which was dehydrogenated to the beta-carboline (V) using sulfur in refluxing xylene. The ester group of (V) was finally reduced to the target alcohol with LiAlH4 in THF.
| 【1】 Srivastava, S.K.; et al.; Potent 1,3-disubstituted-9H-pyrido[3,4-b]indoles as new lead compounds in antifilarial chemotherapy. J Med Chem 1999, 42, 9, 1667. |
| 【2】 Srivastava, S.K.; et al.; Potent 1,3-disubstituted-9H-pyrido[3,4-b]indoles as new lead compounds in antifilarial chemotherapy. Bioorg Med Chem 1999, 7, 6, 1223. |
| 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) | 30836 | L-tryptophan | 73-22-3 | C11H12N2O2 | 详情 | 详情 |
| (II) | 30837 | methyl (2S)-2-amino-3-(1H-indol-3-yl)propanoate | C12H14N2O2 | 详情 | 详情 | |
| (III) | 29029 | 4-chlorobenzaldehyde | 104-88-1 | C7H5ClO | 详情 | 详情 |
| (IV) | 30834 | methyl 1-(4-chlorophenyl)-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylate | C19H17ClN2O2 | 详情 | 详情 | |
| (V) | 30835 | methyl 1-(4-chlorophenyl)-9H-beta-carboline-3-carboxylate | C19H13ClN2O2 | 详情 | 详情 |
Extended Information