Water → HCID 67015552, compound

HRID 1617733Notes

Reaction equation

HRID 1617733 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:9]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH3:27])[CH2:10][C:11]([C:13]1[CH:14]=[CH:15][C:16](=[O:20])[N:17]([CH3:19])[CH:18]=1)=[O:12].[CH2:28]([O:30][C:31](=[O:34])[CH2:32]Br)[CH3:29].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C(=O)C>[CH2:28]([O:30][C:31](=[O:34])[CH2:32][O:8][C:6]1[CH:5]=[CH:4][C:3]([CH:9]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[CH2:10][C:11]([C:13]2[CH:14]=[CH:15][C:16](=[O:20])[N:17]([CH3:19])[CH:18]=2)=[O:12])=[C:2]([F:1])[CH:7]=1)[CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 66668205HCID 66668205, compound

Product 1

HCID 67015552HCID 67015552, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a stirred solution of 5-[3-(2-fluoro-4-hydroxy-phenyl)-3-o-tolyl-propionyl]-1-methyl-1H-pyridin-2-one (71 mg) in N,N-dimethylacetamide (1.5 ml) were added ethylbromoacetate (36 mg) and cesium carbonate (69 mg). The mixture was stirred for 3.5 h at room temperature. Water was added and the mixture was extracted with diethyl ether. The organic phase was dried (MgSO4), filtered and concentrated to dryness. The product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 1:0 to 0:1) to give the title compound (77 mg) as a light brown oil, MS (ESI+): m/z=452.2 [M+H]+.

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 1:0 to 0:1)

Sources & evidence

ORD record
ord-d856d30d43f041d69d5f42aa7a8f7e9b
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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