Cesium carbonate → 2,2-Dimethyl-3-(4-{2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-propionic acid methyl ester

HRID 1985174Notes

Reaction equation

HRID 1985174 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]([CH3:14])([CH3:13])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[CH3:16][N:17]1[CH:21]([CH2:22][CH2:23]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:20][N:19]([CH2:35][C:36]2[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][CH:37]=2)[C:18]1=[O:46].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:15])[C:4]([CH3:13])([CH3:14])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:23][CH2:22][CH:21]2[CH2:20][N:19]([CH2:35][C:36]3[CH:41]=[CH:40][C:39]([C:42]([F:44])([F:45])[F:43])=[CH:38][CH:37]=3)[C:18](=[O:46])[N:17]2[CH3:16])=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 53750180HCID 53750180, compoundHCID 86596229HCID 86596229, compound

Product 1

HCID 688672152,2-Dimethyl-3-(4-{2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-propionic acid methyl esterYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-(4-Hydroxy-phenyl)-2,2-dimethyl-propionic acid methyl ester (31 mg, 0.15 mmol) and Toluene-4-sulfonic acid 2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethyl ester (75 mg, 0.16 mmol) in DMF (1 ml) is added Cs2CO3 (64 mg, 0.19 mmol), and the mixture heated at 60° C. for 15 hours. The mixture is cooled, diluted with water (25 ml) and extracted with ethyl acetate (2×25 ml). The combined organic extracts were washed with brine (25 ml), dried (Na2SO4), and concentrated to an oil. Purification by flash chromatography on a Biotage silica cartridge (gradient elution, 2:1 hexanes:ethyl acetate to 1:4 hexanes:ethyl acetate) produced an oil (69 mg, 94%).

Workup

  1. temperatureThe mixture is cooled
  2. extractionextracted with ethyl acetate (2×25 ml)
  3. washThe combined organic extracts were washed with brine (25 ml)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to an oil
  6. customPurification by flash chromatography
  7. washon a Biotage silica cartridge (gradient elution, 2:1 hexanes:ethyl acetate to 1:4 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-8aec3df40e774b789961a2812885ab8f
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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