【结 构 式】 |
【分子编号】24042 【品名】ethyl 4-phenyl-2-[(1,4,4-trimethyl-2,3-dioxopentyl)amino]butanoate 【CA登记号】 |
【 分 子 式 】C20H29NO4 【 分 子 量 】347.4546 【元素组成】C 69.14% H 8.41% N 4.03% O 18.42% |
合成路线1
该中间体在本合成路线中的序号:(III)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 |