Dimethylformamide → Acetoxymethyl methyl 4-(2',3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 1598795

反応式

HRID 1598795 の反応式
[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].[C:24](=[O:27])([OH:26])[O-].[Na+].[C:29]([O:32][CH2:33]Cl)(=[O:31])[CH3:30].[CH3:35]N(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:24]([O:26][CH3:35])=[O:27])=[C:4]([CH3:23])[NH:3][C:2]([CH3:1])=[C:7]1[C:8]([O:10][CH2:33][O:32][C:29](=[O:31])[CH3:30])=[O:9]

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 69366Chloromethyl acetateHCID 516892Sodium BicarbonateHCID 668096561,4-Dihydro-2,6-dimethyl-4-(2',3'-dichorophenyl)-5-carboxymethyl-3-pyridinecarboxylic acid

生成物 1

HCID 70148229Acetoxymethyl methyl 4-(2',3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate収率 48%

反応条件

温度
80 °C

実験手順

To a stirred mixture of 1,4-dihydro-2,6-dimethyl-4-(2',3'-dichorophenyl)-5-carboxymethyl-3-pyridinecarboxylic acid (0.3 g, 0.83 mmol) and sodium bicarbonate (0.14 g, 1.69 mmol)in DMF (15 ml) under nitrogen atmosphere was added chloromethyl acetate (0.137 g, 1.26 mmol). The reaction mixture was heated at 80° C. for 18 h. Workup by evaporation of solvent and addition of water. Extraction with dichloromethane, the extract was dried over sodium sulfate and concentrated. The resulting oil was subjected to flash chromatography [silica gel, dichloromethane--dichloromethane/methanol (9/1) gradient] to give colorless crystals (0.17 g, 48%) mp. 144.5°-147.6° C. 1H-NMR (CDCl3): 7.30-7.04 (Ar, 3H); 5.97 (s, 1H); 5.73 (d, J=5.5 Hz, 1H); 5.69 (d, J=5.5 Hz, 1H); 5.46 (s, 1H); 3.6 (s, 3H); 2.32 (s, 3H); 2.30 (s, 3H); 2.03 (s, 3H). 13 C-NMR (CDCl3): 169.64; 167.63; 165.81; 147.46; 146.77; 143.85; 132.86; 131.15; 129.83; 128.31; 126.98; 103.97; 101.89; 78.73; 50.93; 38.45; 20.80; 19.86; 19.26.

後処理

  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

出典と根拠

ORDレコード
ord-cda8481865be49bfac0904d1b0ea53d9
出典データセット
uspto-grants-1998_04
特許番号
US05739152

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