Potassium Carbonate → HCID 19354644, compound

HRID 377557Notes

Reaction equation

HRID 377557 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]([F:40])([F:39])[C:9]1[CH:10]=[C:11]([NH:15][C:16](=[O:38])[C:17]([N:20]2[C:25](=[O:26])[C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[C:23]([CH2:33][O:34]C(=O)C)[O:22][CH2:21]2)([CH3:19])[CH3:18])[CH:12]=[CH:13][CH:14]=1>O.CO>[F:40][C:8]([F:7])([F:39])[C:9]1[CH:10]=[C:11]([NH:15][C:16](=[O:38])[C:17]([N:20]2[C:25](=[O:26])[C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[C:23]([CH2:33][OH:34])[O:22][CH2:21]2)([CH3:18])[CH3:19])[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 19354637HCID 19354637, compound

Product 1

HCID 19354644HCID 19354644, compoundYield 42.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of potassium carbonate (0.33 g) in water was added portionwise to a stirred solution of N-(3-trifluoromethylphenyl)-2-(6-acetoxymethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide (0.8 g) in methanol. Stirring was continued for 4 hours at room temperature, the mixture evaporated and the residue dissolved in a mixture of ether and water. The organic layer was dried (magnesium sulphate), evaporated and the residue purified by dry column chromatography eluting with ether to give N-(3-trifluoromethylphenyl)-2-(2,3-dihydro-6-hydroxymethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide (compound 102, 0.31 g) as a gum, NMR (CDCl3)δ 1.7(s,6H), 4.1(d,2H), 5.3(s,2H), 7.1-7.3(m,7H), 7.55(m,1H), 7.75(m,1H), 8.3(s,1H).

Workup

  1. customthe mixture evaporated
  2. dissolutionthe residue dissolved in a mixture of ether and water
  3. dry with materialThe organic layer was dried (magnesium sulphate)
  4. customevaporated
  5. customthe residue purified
  6. customby dry column chromatography
  7. washeluting with ether

Sources & evidence

ORD record
ord-67dd88ffc0874aeab4b49b06011f39b8
Source dataset
uspto-grants-2000_02
Patent number
US06028032

Reaction notes

Loading…