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【结 构 式】 
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【分子编号】24045 【品名】benzyl 2-(2-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]propanoyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate 【CA登记号】 |
【 分 子 式 】C34H40N2O7 【 分 子 量 】588.70088 【元素组成】C 69.37% H 6.85% N 4.76% O 19.02% |
合成路线1
该中间体在本合成路线中的序号：(VI)The condensation of tert-butylalanine (I) with ethyl 2-bromo-4-phenylbutanoate (II) by means of triethylamine in hot DMF gives N-[1-(ethoxycarbonyl)-3-phenylpropyl]alanine tert-butyl ester (III), which is hydrolyzed with trifluoroacetic acid to the corresponding N-substituted alanine (IV). The condensation of (IV) with benzyl 1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline-3-carboxylate (V) by means of triethylamine, 1-hydroxybenzotriazole (HBT) and dicyclohexylcarbodiimide (DCC) in methylene chloride affords benzyl 2-[N-[1-(ethoxycarbonyl)-3-phenylpropyl]alanyl]-1,2,3,4-tetrahydro-6,7-di-methoxyisoquinoline-3-carboxylate (VI), which is finally debenzylated by hydrogenation with H2 over Pd/C in THF.
| 【1】 Hoefle, M.L.; Klutchko, S. (Pfizer Inc.); Substituted acyl derivatives of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids. DD 201787; EP 0049605; EP 0096157; US 4344949 . |
| 【2】 Prous, J.; Castaner, J.; CI-925. Drugs Fut 1986, 11, 4, 257. |
| 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) | 24040 | 5-amino-2,2-dimethyl-3,4-hexanedione | C8H15NO2 | 详情 | 详情 | |
| (II) | 20810 | ethyl 2-bromo-4-phenylbutanoate | C12H15BrO2 | 详情 | 详情 | |
| (III) | 24042 | ethyl 4-phenyl-2-[(1,4,4-trimethyl-2,3-dioxopentyl)amino]butanoate | C20H29NO4 | 详情 | 详情 | |
| (IV) | 24043 | N-[1-(ethoxycarbonyl)-3-phenylpropyl]alanine | C15H21NO4 | 详情 | 详情 | |
| (V) | 24044 | benzyl 6,7-dimethoxy-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate | C19H21NO4 | 详情 | 详情 | |
| (VI) | 24045 | benzyl 2-(2-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]propanoyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate | C34H40N2O7 | 详情 | 详情 |