Citric Acid → 3-(4-{Acetyl[(2',6'-dimethylbiphenyl-3-yl)methyl]amino}phenyl)propanoic acid

HRID 508024Notes

Reaction equation

HRID 508024 reaction equation
[C:1]([N:4]([CH2:17][C:18]1[CH:19]=[C:20]([C:24]2[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:31])[CH:21]=[CH:22][CH:23]=1)[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]([O:15]C)=[O:14])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[OH-].[Na+].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.O1CCCC1>[C:1]([N:4]([CH2:17][C:18]1[CH:19]=[C:20]([C:24]2[C:25]([CH3:31])=[CH:26][CH:27]=[CH:28][C:29]=2[CH3:30])[CH:21]=[CH:22][CH:23]=1)[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 23157605Methyl 3-(4-{acetyl[(2',6'-dimethylbiphenyl-3-yl)methyl]amino}phenyl)propanoate

Product 1

HCID 231575773-(4-{Acetyl[(2',6'-dimethylbiphenyl-3-yl)methyl]amino}phenyl)propanoic acidYield 69.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(4-{acetyl[(2′,6′-dimethylbiphenyl-3-yl)methyl]amino}phenyl)propanoate (0.644 g, 1.55 mmol) in a mixture of methanol (8 mL) and tetrahydrofuran (8 mL) was added 2 M aqueous sodium hydroxide solution (2.5 mL), and the mixture was stirred at room temperature for 18 hr. Water was added to the reaction mixture, and the mixture was weakly acidified with 10% aqueous citric acid solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was recrystallized from ethyl acetate to give the title compound (0.430 g, yield 69%) as colorless prism crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-0fe5b1aa7ac5482698f2840512f77ab3
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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