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

HRID 1985239Notes

Reaction equation

HRID 1985239 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]([CH3:30])=[C:26]([CH3:31])[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][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][C:27]=1[CH3:30])[CH2:23][N:21]1[CH2:22][CH:18]([CH2:17][CH2:16][O:15][C:12]2[CH:11]=[CH:10][C:9]([O:8][C:5]([CH3:7])([CH3:6])[C:4]([OH:34])=[O:3])=[CH:14][CH:13]=2)[N:19]([CH3:33])[C:20]1=[O:32]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 577190842-(4-{2-[1-(3,4-Dimethyl-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid ethyl ester

Product 1

HCID 577189442-(4-{2-[1-(3,4-Dimethyl-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acidYield 54.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(4-{2-[1-(3,4-dimethyl-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid ethyl ester (0.098 g, 0.209 mmol) in ethanol (8 mL) was treated with aqueous 5 N NaOH (0.5 mL) and heated to reflux 1 h. The reaction mixture was cooled, the solvent removed in vacuo. The resultant residue was acidified with aqueous 1 N HCl (5 mL) and extracted with Et2O. The organic layer was dried (MgSO4) and the solvent removed in vacuo to afford 0.050 g (54%) 2-(4-{2-[1-(3,4-dimethyl-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid. HRMS (ES+) m/z exact mass calcd for C25H33N2O5 [M+1] 4.41.2389, found 441.2390. 1H NMR.

Workup

  1. temperatureheated
  2. temperatureto reflux 1 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-47b82b9be7854f2bb18b96f37d3374ee
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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