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

HRID 341868

Reaktionsgleichung

Reaktionsgleichung von HRID 341868
[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]

Komponenten

5

Edukt 4

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

Produkt 1

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

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 (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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-dc02446c467a452b9ae3ee3df52f4706
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05856346

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