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

HRID 508022Notes

Reaction equation

HRID 508022 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]([CH2:29][CH2:30][CH3:31])[C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([O:27]C)=[O:26])=[CH:19][CH:18]=2)[CH:10]=1.[OH-].[Na+].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.O1CCCC1>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]([CH2:29][CH2:30][CH3:31])[C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:21][CH:22]=2)[CH:10]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 23157276Methyl 3-{4-[[(2',6'-dimethylbiphenyl-3-yl)methyl](propyl)amino]phenyl}propanoate

Product 1

HCID 231572523-{4-[[(2',6'-Dimethylbiphenyl-3-yl)methyl](propyl)amino]phenyl}propanoic acidYield 99.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-{4-[[(2′,6′-dimethylbiphenyl-3-yl)methyl](propyl)amino]phenyl}propanoate (0.735 g, 1.77 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 19 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 sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20%-70% ethyl acetate/hexane) to give the title compound (0.710 g, yield 99%) as a yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (20%-70% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-86ae48b9775544089406e92e1cdb102e
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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