Hydrochloric Acid → HCID 57719026, compound

HRID 1985229Notes

Reaction equation

HRID 1985229 reaction equation
C([O:3][C:4](=[O:37])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][C:18]2[N:19]([CH2:34][CH2:35][CH3:36])[C:20](=[O:33])[N:21]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[C:27]([CH3:32])[CH:26]=3)[C:22]=2[CH3:23])=[CH:11][CH:10]=1)([CH3:7])[CH3:6])C.[OH-].[Na+].Cl>CCO>[CH3:32][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][C:28]=1[CH3:31])[CH2:24][N:21]1[C:22]([CH3:23])=[C:18]([CH2:17][CH2:16][CH2:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][C:5]([CH3:6])([CH3:7])[C:4]([OH:37])=[O:3])=[CH:10][CH:11]=2)[N:19]([CH2:34][CH2:35][CH3:36])[C:20]1=[O:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57719025HCID 57719025, compound

Product 1

HCID 57719026HCID 57719026, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(4-{3-[1-(3,4-dimethyl-benzyl)-5-methyl-2-oxo-3-propyl-2,3-dihydro-1H-imidazol-4-yl]-propyl}-phenoxy)-2-methyl-propionic acid ethyl ester (0.124 g, 0.244 mmol) in EtOH (10 mL) was treated with aqueous 5 N NaOH (0.5 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. The mixture was extracted with Et2O and water, the organic layer dried (MgSO4), and the solvent removed in vacuo to afford 0.104 g (89%) 2-(4-{3-[1-(3,4-dimethyl-benzyl)-5-methyl-2-oxo-3-propyl-2,3-dihydro-1H-imidazol-4-yl]-propyl}-phenoxy)-2-methyl-propionic acid. HRMS (ES+) m/z exact mass calcd for C29H39N2O4 [M+1] 479.2910, found 479.2917. 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-9e9ea03ee82b4156a5362a086a0ef357
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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