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

HRID 1985267Notes

Reaction equation

HRID 1985267 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C:5]([CH3:21])([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([OH:13])[CH:8]=1)[CH3:2].[CH3:23][N:24]1[CH:28]([CH2:29][CH2:30]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:27][N:26]([CH2:42][C:43]2[CH:48]=[CH:47][C:46]([C:49]([F:52])([F:51])[F:50])=[CH:45][CH:44]=2)[C:25]1=[O:53].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:22])[C:5]([CH3:21])([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:49]([F:52])([F:51])[F:50])=[CH:17][CH:16]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:30][CH2:29][CH:28]2[CH2:27][N:26]([CH2:42][C:43]3[CH:48]=[CH:47][C:46]([C:49]([F:52])([F:51])[F:50])=[CH:45][CH:44]=3)[C:25](=[O:53])[N:24]2[CH3:23])[CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 688673493-(3-Hydroxy-phenyl)-2-methyl-2-phenoxy-propionic acid ethyl esterHCID 86596229HCID 86596229, compound

Product 1

HCID 865962322-Methyl-3-(3-{2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-2-(4-trifluoromethyl-phenoxy)-propionic acid ethyl esterYield 116.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 3-(3-hydroxy-phenyl)-2-methyl-2-phenoxy-propionic acid ethyl ester (0.100 g, 0.271 mmol), toluene-4-sulfonic acid 2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethyl ester (0.136 g, 0.298 mmol) and Cs2CO3 (0.133 g, 0.408 mmol) in DMF (8 mL) was heated to 65° C. under N2 for 17 h. The reaction was cooled and quenched with 1 N HCl (10 mL) and worked up extractively with Et2O and water. The organic layer was dried (MgSO4) and the solvent removed in vacuo to afford crude product that was purified by flash chromatography using 4:1 hexanes:acetone to afford 0.113 g (64%) 2-methyl-3-(3-{2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-2-(4-trifluoromethyl-phenoxy)-propionic acid ethyl ester. 1H NMR. MS (ES+) Calc'd for C33H35N2O5F6 (M +1) 653. Found m/z 653 (100%).

Workup

  1. temperatureThe reaction was cooled
  2. customquenched with 1 N HCl (10 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customto afford crude product that
  6. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-0962a6a89b824d99b90173b8787302e2
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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