Hydrochloric Acid → 2-Methyl-3-(3-{2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-2-phenoxy-propionic acid

HRID 1985206Notes

Reaction equation

HRID 1985206 reaction equation
C([O:3][C:4](=[O:42])[C:5]([CH3:41])([O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][CH2:15][CH:16]2[CH2:20][N:19]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)[C:18](=[O:32])[N:17]2[CH3:33])[CH:8]=1)C.[OH-].[Na+].Cl>CO>[CH3:41][C:5]([O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][CH2:15][CH:16]2[CH2:20][N:19]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:29])[F:30])=[CH:24][CH:23]=3)[C:18](=[O:32])[N:17]2[CH3:33])[CH:8]=1)[C:4]([OH:42])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 688674542-Methyl-3-(3-{2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-2-phenoxy-propionic acid ethyl ester

Product 1

HCID 688698442-Methyl-3-(3-{2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-2-phenoxy-propionic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the ester obtained from Step A (72 mg, 0.12 mmol) in methanol (2 ml) is added 5N NaOH (0.5 ml, 2.5 mmol), and the mixture stirred for 20 hours at ambient temperature. The mixture is poured into 1N HCl (20 ml), then extracted with ethyl acetate (2×15 ml). The combined ethyl acetate extracts were washed with water, brine, dried (Na2SO4), and concentrated to an oil (64 mg, 94%) (diastereomer 4).

Workup

  1. extractionextracted with ethyl acetate (2×15 ml)
  2. washThe combined ethyl acetate extracts were washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated to an oil (64 mg, 94%) (diastereomer 4)

Sources & evidence

ORD record
ord-081a479b8a084cabbbc4fbc5dfe2b199
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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