Hydrochloric Acid → HCID 57719072, compound

HRID 1985221Notes

Reaction equation

HRID 1985221 reaction equation
C([O:3][C:4](=[O:35])[C:5]([CH3:34])([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][C:17]2[N:18]([CH2:31][CH2:32][CH3:33])[C:19](=[O:30])[N:20]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)[CH:21]=2)=[CH:10][CH:9]=1)[CH3:6])C.[OH-].[Na+].Cl>CCO>[CH3:34][C:5]([O:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:15][CH2:16][C:17]2[N:18]([CH2:31][CH2:32][CH3:33])[C:19](=[O:30])[N:20]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)[CH:21]=2)=[CH:12][CH:13]=1)([CH3:6])[C:4]([OH:35])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 688673762-methyl-2-(4-{2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-2,3-dihydro-1H-imidazol-4-yl]-ethoxy}-phenoxy)-propionic acid ethyl ester

Product 1

HCID 57719072HCID 57719072, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The 2-methyl-2-(4-{2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-2,3-dihydro-1H-imidazol-4-yl]-ethoxy}-phenoxy)-propionic acid ethyl ester (0.036 g, 0.075 mmol) was combined with aqueous 5 N NaOH (0.15 mL) in EtOH (5 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 (1 mL). The mixture was extracted with Et2O and water, the organic layer dried (MgSO4), and the solvent removed in vacuo to afford 0.024 g (71%) 2-methyl-2-(4-{2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-2,3-dihydro-1H-imidazol-4-yl]-ethoxy}-phenoxy)-propionic acid. HRMS (ES+) m/z exact mass calcd for C26H33N2O5 [M+0.1] 453.2389, found 453.2387. 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-d9636fc382da42e0a61a0e57f900b5ef
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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