Hydrochloric Acid → 3-[3-phenyl-1-[3-[2-(2-pyridyl)ethylaminocarbonyl]benzyl]-1H-pyrazol-4-yl]propionic acid

HRID 350145Notes

Reaction equation

HRID 350145 reaction equation
[C:1]1([C:7]2[C:11]([CH2:12][CH2:13][C:14]([O:16]CC)=[O:15])=[CH:10][N:9]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([NH:28][CH2:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=4)=[O:27])[CH:21]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].C(O)C.Cl>O1CCCC1>[C:1]1([C:7]2[C:11]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:10][N:9]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([NH:28][CH2:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=4)=[O:27])[CH:21]=3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 23024725ethyl 3-[3-phenyl-1-[3-[2-(2-pyridyl)ethylaminocarbonyl)benzyl]-1H-pyrazol-4-yl]propionate

Product 1

HCID 694239263-[3-phenyl-1-[3-[2-(2-pyridyl)ethylaminocarbonyl]benzyl]-1H-pyrazol-4-yl]propionic acidYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 3-[3-phenyl-1-[3-[2-(2-pyridyl)ethylaminocarbonyl]benzyl]-1H-pyrazol-4-yl]propionate (450 mg), 1 N aqueous sodium hydroxide solution (2 ml), ethanol (2 ml), and tetrahydrofuran (2 ml) was stirred at room temperature for one hour. After 1 N hydrochloric acid (2 ml) was added to the reaction mixture, the reaction mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The obtained crystals were collected by filtration, and 3-[3-phenyl-1-[3-[2-(2-pyridyl)ethylaminocarbonyl]benzyl]-1H-pyrazol-4-yl]propionic acid (400 mg, yield: 95%) was obtained. This was recrystallized from tetrahydrofuran-hexane. Melting point: 166–167° C.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. filtrationThe obtained crystals were collected by filtration

Sources & evidence

ORD record
ord-3c5a62c157104c4ebf7af83b73a122ae
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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