Hydrochloric Acid → 2-methyl-3-(4-{2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-2,3-dihydro-1H-imidazol-4-yl]-ethoxy}-phenyl)-2-phenoxy-propionic acid

HRID 1985225Notes

Reaction equation

HRID 1985225 reaction equation
C([O:3][C:4](=[O:41])[C:5]([CH3:40])([O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[N:17]([CH2:30][CH2:31][CH3:32])[C:18](=[O:29])[N:19]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)[CH:20]=2)=[CH:9][CH:8]=1)C.[OH-].[Na+].Cl>CCO>[CH3:40][C:5]([O:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH2:15][C:16]2[N:17]([CH2:30][CH2:31][CH3:32])[C:18](=[O:29])[N:19]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=3)[CH:20]=2)=[CH:11][CH:12]=1)[C:4]([OH:41])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 688668192-methyl-3-(4-{2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-2,3-dihydro-1H-imidazol-4-yl]-ethoxy}-phenyl)-2-phenoxy-propionic acid ethyl ester

Product 1

HCID 688675222-methyl-3-(4-{2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-2,3-dihydro-1H-imidazol-4-yl]-ethoxy}-phenyl)-2-phenoxy-propionic acidYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The 2-methyl-3-(4-{2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-2,3-dihydro-1H-imidazol-4-yl]-ethoxy}-phenyl)-2-phenoxy-propionic acid ethyl ester (0.011 g, 0.020 mmol) was combined with aqueous 5 N NaOH (0.2 mL) in EtOH (3 mL) and heated to reflux under N2 for 1 h. The reaction was cooled and the solvent removed in vacuo to give a residue that was acidified with aqueous 1 N HCl (2 mL). The mixture was extracted with Et2O and water, the organic layer dried (MgSO4), and the solvent removed in vacuo to afford 0.007 g (67%) 2-methyl-3-(4-{2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-2,3-dihydro-1H-imidazol-4-yl]-ethoxy}-phenyl)-2-phenoxy-propionic acid. HRMS (ES+) m/z exact mass calcd for C32H37N2O5 [M+1] 529.2702, found 529.2715. 1H NMR.

Workup

  1. temperatureheated
  2. temperatureto reflux under N2 for 1 h
  3. temperatureThe reaction was cooled
  4. customthe solvent removed in vacuo
  5. customto give a residue that
  6. extractionThe mixture was extracted with Et2O and water
  7. dry with materialthe organic layer dried (MgSO4)
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-69e5274141ac48c080f9b487b4d650c5
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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