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

HRID 341867

反応式

HRID 341867 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].[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

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 (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.

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-bd3ce38fef59482aa6f099b6adca1d9e
出典データセット
uspto-grants-1999_01
特許番号
US05856346

関連ノート

読み込み中…