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

HRID 350141Notes

Reaction equation

HRID 350141 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][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=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][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=4)=[O:27])[CH:21]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 23025042ethyl 3-[3-phenyl-1-[3-(2-picolylaminocarbonyl)benzyl]-1H-pyrazol-4-yl]propionate

Product 1

HCID 694255183-[3-phenyl-1-[3-(2-picolylaminocarbonyl)benzyl]-1H-pyrazol-4-yl]propionic acidYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 3-[3-phenyl-1-[3-(2-picolylaminocarbonyl)benzyl]-1H-pyrazol-4-yl]propionate (180 mg), 1 N aqueous sodium hydroxide solution (0.77 ml), ethanol (1 ml), and tetrahydrofuran (1 ml) was stirred at room temperature for one hour. 1 N hydrochloric acid (0.77 ml) was added to the reaction mixture, which 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-picolylaminocarbonyl)benzyl]-1H-pyrazol-4-yl]propionic acid (120 mg, yield: 71%) was obtained. This was recrystallized from ethyl acetate-hexane. Melting point: 83–85° C. (decomposition).

Workup

  1. extractionwas 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-14c0e1eb9d4a449ab9014293e33271bd
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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