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

HRID 1985223Notes

Reaction equation

HRID 1985223 reaction equation
C([O:3][C:4](=[O:36])[C:5]([O:34][CH3:35])([CH3:33])[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>[CH3:35][O:34][C:5]([CH3:33])([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:36])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68868070HCID 68868070, compound

Product 1

HCID 688667972-methoxy-2-methyl-3-(4-{2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-2,3-dihydro-1H-imidazol-4-yl]-ethoxy}-phenyl)-propionic acidYield 103.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The 2-methoxy-2-methyl-3-(4-{2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-2,3-dihydro-1H-imidazol-4-yl]-ethoxy}-phenyl)-propionic acid ethyl ester (0.015 g, 0.031 mmol) was combined with aqueous 5 N NaOH (0.1 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 (3 mL). The mixture was extracted with Et2O and water, the organic layer dried (MgSO4), and the solvent removed in vacuo to afford 0.015 g (100%) 2-methoxy-2-methyl-3-(4-{2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-2,3-dihydro-1H-imidazol-4-yl]-ethoxy}-phenyl)-propionic acid. MS (ES+) m/z calcd for C26H32N2O5 [M+1] 453, found 453. 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-a7ff4ce7d5c7464a8660fad02699410f
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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