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

HRID 1985113Notes

Reaction equation

HRID 1985113 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH:4]([O:13][CH:14]([CH3:16])[CH3:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[CH3:18][O:19][C:20]1[CH:46]=[CH:45][C:23]([CH2:24][N:25]2[CH2:29][CH:28]([CH2:30][CH2:31]OS(C3C=CC(C)=CC=3)(=O)=O)[N:27]([CH3:43])[C:26]2=[O:44])=[CH:22][CH:21]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:17])[CH:4]([O:13][CH:14]([CH3:15])[CH3:16])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:31][CH2:30][CH:28]2[CH2:29][N:25]([CH2:24][C:23]3[CH:45]=[CH:46][C:20]([O:19][CH3:18])=[CH:21][CH:22]=3)[C:26](=[O:44])[N:27]2[CH3:43])=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 149239963-(4-Hydroxyphenyl)-2-isopropoxypropanoic acid methyl esterHCID 57719164Toluene-4-sulfonic acid 2-[1-(4-methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethyl ester

Product 1

HCID 688674612-Isopropoxy-3-(4-{2-[1-(4-methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-propionic acid methyl esterYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

3-(4-Hydroxy-phenyl)-2-isopropoxy-propionic acid methyl ester (1.7 g, 7.3 mmol), Toluene-4-sulfonic acid 2-[1-(4-methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethyl ester (3.4 g, 8.0 mmol), and Cs2CO3 (3.6 g, 11 mmol) were combined in 10 mL of DMF and heated at 55° C. for 18 h. After cooling, the mixture is diluted with 100 mL of water and extracted with 3×20 mL of ethyl acetate. The organics were dried, concentrated, and the residue is purified by flash chromatography using 7/3 ethyl actate/hexanes to give 3.0 g (86%) of the title compound as an oil. NMR

Workup

  1. temperatureAfter cooling
  2. extractionextracted with 3×20 mL of ethyl acetate
  3. customThe organics were dried
  4. concentrationconcentrated
  5. customthe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-21786fef71ce4728863b98731025f18a
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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