2-[(3,3-diphenylpropyl)(methyl)amino]-1,1-dimethylethyl (Z)-2-acetyl-3-(3-nitrophenyl)-2-propenoate -Drug Synthesis Database

【结构式】

【分子编号】17751

【品名】2-[(3,3-diphenylpropyl)(methyl)amino]-1,1-dimethylethyl (Z)-2-acetyl-3-(3-nitrophenyl)-2-propenoate

【CA登记号】

【分子式】C₃₁H₃₄N₂O₅

【分子量】514.62144

【元素组成】C 72.35% H 6.66% N 5.44% O 15.54%

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：(V)

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.

参考文献中间体

合成目标

【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

Extended Information