Sodium Hydroxide → HCID 68867616, compound

HRID 1985208Notes

Reaction equation

HRID 1985208 reaction equation
C([O:3][C:4](=[O:42])[C:5]([CH3:41])([O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH:16]2[CH2:20][N:19]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)[C:18](=[O:32])[N:17]2[CH3:33])=[CH:9][CH:8]=1)C.[OH-].[Na+]>C(O)C>[CH3:41][C:5]([O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH:16]2[CH2:20][N:19]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)[C:18](=[O:32])[N:17]2[CH3:33])=[CH:9][CH:8]=1)[C:4]([OH:42])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68867285HCID 68867285, compound

Product 1

HCID 68867616HCID 68867616, compoundYield 105.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-methyl-3-(4-{3-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-propyl}-phenyl)-2-phenoxy-propionic acid ethyl ester (0.062 g, 0.106 mmol) in ethanol (8 mL) is treated with aqueous 5 N NaOH (1 mL) and heated to reflux 1 h. The reaction mixture is cooled, the solvent removed in vacuo. The resultant residue is acidified with aqueous 1 N HCl (20 mL) and extracted with CH2Cl2. The organic layer is dried (Na2SO4) and the solvent removed in vacuo to afford 0.062 g (100%) 2-methyl-3-(4-{3-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-propyl}-phenyl)-2-phenoxy-propionic acid. 1H NMR. HRMS (ES+) m/z exact mass calc'd for C31H34N2O4F3 (M+1) 555.2471. Found m/z 555.2459.

Workup

  1. temperatureheated
  2. temperatureto reflux 1 h
  3. temperatureThe reaction mixture is cooled
  4. customthe solvent removed in vacuo
  5. extractionextracted with CH2Cl2
  6. dry with materialThe organic layer is dried (Na2SO4)
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-36c876d5066b4be6b27eb09c717afa99
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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