Sodium Hydroxide → 2-(4-{2-[1-(4-Methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid

HRID 1985233Notes

Reaction equation

HRID 1985233 reaction equation
C([O:3][C:4](=[O:34])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH:18]2[CH2:22][N:21]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[C:20](=[O:32])[N:19]2[CH3:33])=[CH:11][CH:10]=1)([CH3:7])[CH3:6])C.[OH-].[Na+]>C(O)C>[CH3:31][O:30][C:27]1[CH:26]=[CH:25][C:24]([CH2:23][N:21]2[CH2:22][CH:18]([CH2:17][CH2:16][O:15][C:12]3[CH:11]=[CH:10][C:9]([O:8][C:5]([CH3:7])([CH3:6])[C:4]([OH:34])=[O:3])=[CH:14][CH:13]=3)[N:19]([CH3:33])[C:20]2=[O:32])=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 577188992-(4-{2-[1-(4-Methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid ethyl ester

Product 1

HCID 577191972-(4-{2-[1-(4-Methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acidYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(4-{2-[1-(4-methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid ethyl ester (0.198 g, 0.421 mmol) in ethanol (10 mL) was treated with aqueous 5 N NaOH (1 mL) and heated to reflux 1.5 h. The reaction mixture was cooled, the solvent removed in vacuo. The resultant residue was acidified with aqueous 1 N HCl (10 mL) and extracted with Et2O. The organic layer was dried (MgSO4) and the solvent removed in vacuo to afford 0.147 g (79%) 2-(4-{2-[1-(4-methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid. MS (ES+) Calc'd for C24H31N2O6 (M+1) 443. Found m/z 443 (100%). 1H NMR.

Workup

  1. temperatureheated
  2. temperatureto reflux 1.5 h
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent removed in vacuo
  5. extractionextracted with Et2O
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-9b0afe3458be4e2aa112c3f2770d6cb2
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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