Butanoic acid, 2-[(3-nitrophenyl)methylene]-3-oxo-, 1-methylethyl ester → Azelnidipine

HRID 1713412Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1713412
C[O-].[Na+].[CH:4]([O:7][C:8](=[O:23])[C:9](=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=1)[C:10]([CH3:12])=O)([CH3:6])[CH3:5].C(O)(=O)C.[CH:28]([N:41]1[CH2:44][CH:43]([O:45][C:46](=[O:51])[CH2:47][C:48](=[NH:50])[NH2:49])[CH2:42]1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(O)(C)C>[CH:4]([O:7][C:8]([C:9]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:47]([C:46]([O:45][CH:43]2[CH2:42][N:41]([CH:28]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:44]2)=[O:51])=[C:48]([NH2:49])[NH:50][C:10]=1[CH3:12])=[O:23])([CH3:6])[CH3:5]

Komponenten

5

Edukt 3

HCID 3951175Butanoic acid, 2-[(3-nitrophenyl)methylene]-3-oxo-, 1-methylethyl esterHCID 10942334Sodium MethoxideHCID 453582921-Benzhydrylazetidin-3-YL 3-amino-3-iminopropanoate acetate

Produkt 1

HCID 65948AzelnidipineAusbeute 88,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

According to Japanese Examined Patent Publication (Kokoku) No. Hei 3-31715, sodium methoxide (0.27 g) was added to a solution of 2-(3-nitrobenzylidene)acetoacetic acid isopropyl ester (1.39 g) and amidinoacetic acid (1-benzhydryl-3-azetidinyl) ester acetate (1.62 g) in isopropyl alcohol (80 ml) and the mixture was heated under reflux for 4 hours. After the reaction mixture was cooled, insoluble material was removed and the solvent was evaporated under reduced pressure. The thus obtained residue was dissolved in ethyl acetate and the mixture was washed with water, followed by drying over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was subjected to silica gel column chromatography (toluene:ethyl acetate=3:1) to obtain pale yellow (±)-2-amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 3-(1-diphenylmethylazetidin-3-yl) ester 5-isopropyl ester (2.17 g, 74%).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperatureAfter the reaction mixture was cooled
  4. custominsoluble material was removed
  5. customthe solvent was evaporated under reduced pressure
  6. dissolutionThe thus obtained residue was dissolved in ethyl acetate
  7. washthe mixture was washed with water
  8. dry with materialby drying over anhydrous sodium sulfate
  9. customThe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4f45a28a2d2a4a0c87ad9c6b8c2cd641
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795281B2

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