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【结 构 式】 
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【分子编号】17749 【品名】2-[(3,3-diphenylpropyl)(methyl)amino]-1,1-dimethylethyl 3-oxobutanoate 【CA登记号】 |
【 分 子 式 】C24H31NO3 【 分 子 量 】381.51508 【元素组成】C 75.56% H 8.19% N 3.67% O 12.58% |
合成路线1
该中间体在本合成路线中的序号：(III)Two new related ways for the synthesis of lercanidipine have been reported: 1) The condensation of diketene (I) with the aminoalcohol (II) gives the corresponding acetoacetate ester (III), which is allowed to react with 3-nitrobenzaldehyde (IV) by means of HCl in chloroform yielding the expected benzylidene derivative (V). Finally, this compound is cyclized with methyl 3-aminocrotonate (VI) in refluxing isopropanol. 2) By esterification of 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl ester (VIII) with alcohol (II) by means of SOCl2 in DMF/dichloromethane.
| 【1】 Catto, A.; Motta, G.; Pennini, R.; Testa, R.; Sironi, G.; Cerri, A.; Leonardi, A.; Asymmetric N-(3,3-diphenylpropyl)aminoalkyl esters of 4-aryl-2,6-dimethyl-1,4-dihydropyridine-3, 5-dicarboxylic acids with antihypertensive activity. Eur J Med Chem 1998, 33, 5, 399. |
| 【2】 Nardi, D.; Leonardi, A.; Graziani, G.; Bianchi, G. (Recordati Industria Chimica e Farmaceutica SpA); N-(3,3-diphenylpropyl)aminoethylesters of 1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylic acid, compositions and use. EP 0153016; JP 60199874; US 4772621; US 4968832 . |
| 【3】 Bianchi, G.; Leonardi, A.; REC 15/2375. Drugs Fut 1987, 12, 12, 1113. |
| 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) | 11367 | 4-Methylene-2-oxetanone; Acetyl ketene | 674-82-8 | C4H4O2 | 详情 | 详情 |
| (II) | 17748 | 1-[(3,3-diphenylpropyl)(methyl)amino]-2-methyl-2-propanol | C20H27NO | 详情 | 详情 | |
| (III) | 17749 | 2-[(3,3-diphenylpropyl)(methyl)amino]-1,1-dimethylethyl 3-oxobutanoate | C24H31NO3 | 详情 | 详情 | |
| (IV) | 12646 | 3-Nitrobenzaldehyde | 99-61-6 | C7H5NO3 | 详情 | 详情 |
| (V) | 17751 | 2-[(3,3-diphenylpropyl)(methyl)amino]-1,1-dimethylethyl (Z)-2-acetyl-3-(3-nitrophenyl)-2-propenoate | C31H34N2O5 | 详情 | 详情 | |
| (VI) | 11372 | Methyl (E)-3-amino-2-butenoate; Methyl 3-aminocrotonate | C5H9NO2 | 详情 | 详情 | |
| (VII) | 13950 | 5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydro-3-pyridinecarboxylic acid | C16H16N2O6 | 详情 | 详情 |