Sodium hydride → Propionoxymethyl methyl 4-(2',3'-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 341867

반응식

HRID 341867 반응식
[CH3:1][C:2]1[NH:3][C:4]([CH3:23])=[C:5](CC(O)=O)[CH:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:12]=2[Cl:18])[C:7]=1[C:8]([OH:10])=[O:9].[H-].[Na+].[C:26]([O:30][CH2:31]Cl)(=[O:29])[CH2:27][CH3:28]>CN(C=O)C>[Cl:18][C:12]1[C:13]([Cl:17])=[CH:14][CH:15]=[CH:16][C:11]=1[CH:6]1[C:5]([C:26]([O:30][CH3:31])=[O:29])=[C:4]([CH3:23])[NH:3][C:2]([CH3:1])=[C:7]1[C:8]([O:10][CH2:31][O:30][C:26](=[O:29])[CH2:27][CH3:28])=[O:9]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 221144Chloromethyl propionateHCID 668096561,4-Dihydro-2,6-dimethyl-4-(2',3'-dichorophenyl)-5-carboxymethyl-3-pyridinecarboxylic acid

생성물 1

HCID 9911194Propionoxymethyl methyl 4-(2',3'-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate수율 71.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a stirred mixture of 1,4-dihydro-2,6-dimethyl-4-(2',3'-dichorophenyl)-5-carboxymethyl-3-pyridinecarboxylic acid (5 g,14 mmol) and sodium hydride (0.6 g, 14 mmol) in DMF (25 ml) under nitrogen atmosphere was added chloromethyl propionate (1.71 g, 14 mmol). The reaction mixture was heated at 80° C. for 16 h. Workup by evaporation of solvent and addition of water. Extraction with dichloromethane, the extract was dried over sodium sulfate and concentrated. The resulting yellow crystals was subjected to flash chromatography [silica gel, dichloromethane - dichloromethane/methanol (9/1) gradient] to give pale yellow crystals (2.21 g, 36%), mp.123.8°-125.5° C. 1H-NMR (CDCl3): 7.30-7.03 (Ar, 3H); 5.97 (s, 1H); 5.75 (d, J=5.5 Hz, 1H); 5.72 (d, J=5.5 Hz, 1H); 5.46 (s, 1H); 3.60 (s, 3H); 2.34-2.25 (m, 8H); 1.09 (t, J=7.5 Hz, 3H). 13C-NMR (CDCl3): 173.11; 167.65; 165.83; 147.47; 146.70; 143.87; 132.86; 131.14; 129.83; 128.30; 126.96; 103.95; 101.94; 78.70; 50.92; 38.45; 27.25; 19.86; 19.25; 8.61.

후처리

  1. customWorkup by evaporation of solvent and addition of water
  2. extractionExtraction with dichloromethane
  3. dry with materialthe extract was dried over sodium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-bd3ce38fef59482aa6f099b6adca1d9e
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05856346

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