Sodium Hydroxide → 2-Methyl-2-(4-{3-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-propyl}-phenoxy)-pentanoic acid

HRID 1985252Notes

Reaction equation

HRID 1985252 reaction equation
C([O:3][C:4](=[O:38])[C:5]([CH3:37])([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH:19]2[CH2:23][N:22]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)[C:21](=[O:35])[N:20]2[CH3:36])=[CH:12][CH:11]=1)[CH2:6][CH2:7][CH3:8])C.[OH-].[Na+]>CCO>[CH3:37][C:5]([O:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][CH2:18][CH:19]2[CH2:23][N:22]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([C:31]([F:34])([F:32])[F:33])=[CH:29][CH:30]=3)[C:21](=[O:35])[N:20]2[CH3:36])=[CH:14][CH:15]=1)([CH2:6][CH2:7][CH3:8])[C:4]([OH:38])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 577191102-Methyl-2-(4-{3-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl)-propyl}-phenoxy)-pentanoic acid ethyl ester

Product 1

HCID 577189712-Methyl-2-(4-{3-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-propyl}-phenoxy)-pentanoic acidYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-methyl-2-(4-{3-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-propyl}-phenoxy)-pentanoic acid ethyl ester (0.020 g, 0.040 mmol) and 5 N NaOH (0.5 mL) in EtOH (6 mL) was heated at reflux for 1 h. The reaction mixture was cooled and quenched with 1 N HCl. The mixture was then diluted with water and extracted with CH2Cl2. The organic layer was dried (Na2SO4) and the solvent removed in vacuo to afford 0.010 g (53%) 2-methyl-2-(4-{3-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-propyl}-phenoxy)-pentanoic acid. 1H NMR. HRMS (ES+) m/z exact mass calcd for C27H34N2O4F3 [M+1] 507.2471, found 507.2459.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. temperatureThe reaction mixture was cooled
  4. customquenched with 1 N HCl
  5. additionThe mixture was then diluted with water
  6. extractionextracted with CH2Cl2
  7. dry with materialThe organic layer was dried (Na2SO4)
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-ef9fc5f1f4c34dab816a577a2f3a4f9a
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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