2-Butenoic acid, 3-amino-, 1-methylethyl ester → Isradipine
Reaktionsgleichung
[CH3:1][O:2][C:3](=[O:18])[C:4]([C:15](=O)[CH3:16])=[CH:5][C:6]1[C:11]2=[N:12][O:13][N:14]=[C:10]2[CH:9]=[CH:8][CH:7]=1.[CH:19]([O:22][C:23](=[O:28])/[CH:24]=[C:25](\[NH2:27])/[CH3:26])([CH3:21])[CH3:20]>C(O)C>[CH3:16][C:15]1[NH:27][C:25]([CH3:26])=[C:24]([C:23]([O:22][CH:19]([CH3:21])[CH3:20])=[O:28])[CH:5]([C:6]2[C:11]3=[N:12][O:13][N:14]=[C:10]3[CH:9]=[CH:8][CH:7]=2)[C:4]=1[C:3]([O:2][CH3:1])=[O:18]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To achieve the afore-mentioned objects, the present invention provides for a process for the manufacture of the Isradipine which, involves two steps. In the first step 2,1,3-benzoxadiazole-4-carboxaldehyde is reacted with methyl acetoacetate in the presence of acetic acid and piperidine in diisopropyl ether. The product 2-acetyl-3-benzofurazan-4-yl-acrylic acid methyl ester is isolated and purified to get substantially high purity product with less than 0.3% 2,1,3-benzoxadiazole-4-carboxaldehyde content present in the purified product. In the second step the purified intermediate 2-acetyl-3-benzofurazan-4-yl-acrylic acid methyl ester is reacted with isopropyl-β-aminocrotonate in ethanol at 25 to 35° C. The crude Isradipine is crystallised from ethanol to get pure Isradipine having substantially higher purity and containing lower amount of the symmetrical ester isomers (III) and (IV).