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

HRID 1713412노트

반응식

HRID 1713412 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

HCID 65948Azelnidipine수율 88.2%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-4f45a28a2d2a4a0c87ad9c6b8c2cd641
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795281B2

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