Citric Acid → 3-[4-({4-[(3,5-diphenyl-1H-pyrazol-1-yl)methyl]benzyl}amino)phenyl]propanoic acid

HRID 508038Notes

Reaction equation

HRID 508038 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:9]([CH2:18][C:19]3[CH:38]=[CH:37][C:22]([CH2:23][NH:24][C:25]4[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][C:33]([O:35]C)=[O:34])=[CH:27][CH:26]=4)=[CH:21][CH:20]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.O1CCCC1>[C:1]1([C:7]2[CH:11]=[C:10]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:9]([CH2:18][C:19]3[CH:20]=[CH:21][C:22]([CH2:23][NH:24][C:25]4[CH:26]=[CH:27][C:28]([CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[CH:29][CH:30]=4)=[CH:37][CH:38]=3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 23157561methyl 3-[4-({4-[(3,5-diphenyl-1H-pyrazol-1-yl)methyl]benzyl}amino)phenyl]propanoate

Product 1

HCID 231575943-[4-({4-[(3,5-diphenyl-1H-pyrazol-1-yl)methyl]benzyl}amino)phenyl]propanoic acidYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-[4-({4-[(3,5-diphenyl-1H-pyrazol-1-yl)methyl]benzyl}amino)phenyl]propanoate (100 mg, 0.20 mmol) in methanol (5 mL) and tetrahydrofuran (5 mL) was added 1 M aqueous sodium hydroxide solution (2 mL), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into water, and the mixture was weakly acidified with 10% aqueous citric acid solution and extracted with ethyl acetate. The ethyl acetate layer was dried using a Presep Dehydration tube (manufactured by Wako Pure Chemical Industries, Ltd.), and concentrated. The residue was purified by silica gel column chromatography (20%-80% ethyl acetate/hexane) to give the title compound (75 mg, yield 77%) as colorless crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe ethyl acetate layer was dried
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (20%-80% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-db93fda3cbf54112aa76cc3818b1839d
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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