Dimethylformamide → 3,5-Pyridinedicarboxylic acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, 3-methyl 5-((1-oxobutoxy)methyl) ester

HRID 341868

反応式

HRID 341868 の反応式
[CH3:1][C:2]1[NH:3][C:4]([CH3:23])=[C:5]([CH2:19]C(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)(O)[O-:25].[Na+].[C:29]([O:34][CH2:35]Cl)(=[O:33])[CH2:30][CH2:31][CH3:32].CN(C=[O:41])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:19]([O:25][CH3:24])=[O:41])=[C:4]([CH3:23])[NH:3][C:2]([CH3:1])=[C:7]1[C:8]([O:10][CH2:35][O:34][C:29](=[O:33])[CH2:30][CH2:31][CH3:32])=[O:9]

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 2725008Chloromethyl butanoateHCID 668096561,4-Dihydro-2,6-dimethyl-4-(2',3'-dichorophenyl)-5-carboxymethyl-3-pyridinecarboxylic acid

生成物 1

HCID 1539943,5-Pyridinedicarboxylic acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, 3-methyl 5-((1-oxobutoxy)methyl) ester収率 66%

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 (2.62 g, 7.35 mmol) and sodium bicarbonate (1.26 g, 15 mmol) in DMF (130 ml) under nitrogen atmosphere was added chloromethyl butyrate (1.53 g, 11.21 mmol). The reaction mixture was heated at 80° C. for 24 h. Workup by filtration followed by evaporation of solvent. The crude residue was chromatographed on silica gel with 45% ethyl acetate in isooctane. Recrystallization from diisopropylether gave colorless crystals (2.20 g, 66%), mp. 136.2°-138.5° C. 1H-NMR (CDCl3): 7.30-7.03 (m, 3H); 5.89 (s, 1H); 5.74 (d, J=5.5 Hz, 1H); 5.70 (d, J=5.5 Hz, 1H); 5.46 (s, 1 H); 3.60 (s, 3H); 2.33 (m, 8H); 1.65-1.55 (m, 2H); 0.90 (t, J=7.4 Hz, 3H).13C-NMR (CDCl3): 172.25; 167.61; 165.80; 147.43; 146.59; 143.82; 132.89; 131.11; 129.82; 128.30; 126.95; 103.97; 101.99; 78.63; 50.92; 38.49; 35.79; 19.91; 19.30; 18.01; 13.50.

後処理

  1. filtrationWorkup by filtration
  2. customfollowed by evaporation of solvent
  3. customThe crude residue was chromatographed on silica gel with 45% ethyl acetate in isooctane
  4. customRecrystallization from diisopropylether

出典と根拠

ORDレコード
ord-dc02446c467a452b9ae3ee3df52f4706
出典データセット
uspto-grants-1999_01
特許番号
US05856346

関連ノート

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