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

HRID 1985257Notes

Reaction equation

HRID 1985257 reaction equation
[CH:1]1([O:6][C:7](=[O:23])[CH:8]([O:17][CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:24][N:25]1[CH:29]([CH2:30][CH2:31]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:28][N:27]([CH2:43][C:44]2[CH:49]=[CH:48][C:47]([C:50]([F:53])([F:52])[F:51])=[CH:46][CH:45]=2)[C:26]1=[O:54].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH:1]1([O:6][C:7](=[O:23])[CH:8]([O:17][CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)[CH2:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:31][CH2:30][CH:29]3[CH2:28][N:27]([CH2:43][C:44]4[CH:49]=[CH:48][C:47]([C:50]([F:52])([F:53])[F:51])=[CH:46][CH:45]=4)[C:26](=[O:54])[N:25]3[CH3:24])=[CH:14][CH:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 68869672HCID 68869672, compoundHCID 86596229HCID 86596229, compound

Product 1

HCID 688693802-Cyclopentyloxy-3-(4-{2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-propionic acid cyclopentyl esterYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 2-cyclopentyloxy-3-(4-hydroxy-phenyl)-propionic acid cyclopentyl ester(0.090 g, 0.283 mmol), toluene-4-sulfonic acid 2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethyl ester (0.140 g, 0.307 mmol) and Cs2CO3 (0.138 g, 0.423 mmol) in DMF (10 mL) was heated to 65° C. under N2 for 16 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 3:1 hexanes:acetone to afford 0.108 g (64%) 2-cyclopentyloxy-3-(4-{2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-propionic acid cyclopentyl ester. 1H NMR. MS (ES+) Calc'd for C33H42N2O5F3 (M+1) 603. Found m/z 603 (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-1ba98cce38f944299e52dd808953e5e4
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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