Dimethylformamide → 167356-39-0

HRID 1598797Notes

Reaction equation

HRID 1598797 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:23])=[C:5]([CH2:19]C(O)=O)[C@@H: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+].Cl[CH2:30][O:31][C:32](=[O:36])[CH2:33][CH2:34][CH3:35].CN(C=[O:41])C>>[Cl:18][C:12]1[C:13]([Cl:17])=[CH:14][CH:15]=[CH:16][C:11]=1[C@H: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][CH2:30][O:31][C:32](=[O:36])[CH2:33][CH2:34][CH3:35])=[O:9]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 2725008Chloromethyl butanoateHCID 22884797(4R)-1,4-dihydro-2,6-dimethyl-4-(2',3'-dichorophenyl)-5-carboxymethyl-3-pyridinecarboxylic acid

Product 1

HCID 22884799167356-39-0Yield 70%

Conditions

Temperature
80 °C

Procedure

To a stirred mixture of (4R)-1,4-dihydro-2,6-dimethyl-4-(2',3'-dichorophenyl)-5-carboxymethyl-3-pyridinecarboxylic acid (2.93 g, 8.23 mmol) and sodium bicarbonate (1.38 g, 16.5 mmol)in DMF (150 ml) under nitrogen atmosphere was added chloromethylbutyrate (1.72 g, 12.6 mmol). The reaction mixture was heated at 80° C. for 17 h. Workup by filtration followed by evaporation of solvent. The crude residue was chromatographed on silica gel with 5% ethylacetate in dichloromethane. Recrystallization from diisopropylether gave colorless crystals (2.62 g, 70%), mp. 128°-129° C. NMR spectral data are identical with the data of the racemate as shown for Compound C. [α]D20 =+17.5° (1% in methanol).

Workup

  1. filtrationWorkup by filtration
  2. customfollowed by evaporation of solvent
  3. customThe crude residue was chromatographed on silica gel with 5% ethylacetate in dichloromethane
  4. customRecrystallization from diisopropylether

Sources & evidence

ORD record
ord-a3eae94728c54d09bd4956665ef4cd04
Source dataset
uspto-grants-1998_04
Patent number
US05739152

Reaction notes

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