Dimethylformamide → 167356-39-0

HRID 341869

Reaction equation

HRID 341869 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+].[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[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][CH2:35][O:34][C:29](=[O:33])[CH2:30][CH2:31][CH3:32])=[O:9]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 2725008Chloromethyl butanoateHCID 22884797HCID 22884797, compound

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 chloromethyl butyrate (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% ethyl acetate 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 in Example 3. [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% ethyl acetate in dichloromethane
  4. customRecrystallization from diisopropylether

Sources & evidence

ORD record
ord-87aacaf89f584194a518128384d95ddc
Source dataset
uspto-grants-1999_01
Patent number
US05856346

Linked notes

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