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

HRID 341866

Reaktionsgleichung

Reaktionsgleichung von HRID 341866
[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]

Komponenten

5

Edukt 4

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

Produkt 1

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

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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); 3.60 (s, 3H); 2.32 (s, 3H); 2.30 (s, 3H); 2.03 (s, 3H). 13C-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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-352bbaa958f64446b35c8aea8d16245a
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05856346

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