Sodium Hydroxide → 3-[4-(Cyclohexylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoic acid

HRID 1799366Notes

Reaction equation

HRID 1799366 reaction equation
[CH:1]1([NH:7][C:8]([C:10]2[CH:11]=[N:12][N:13]([C:19]3[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=3)[C:22]([O:24]C)=[O:23])[C:14]=2[S:15][CH2:16][CH2:17][CH3:18])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([NH:7][C:8]([C:10]2[CH:11]=[N:12][N:13]([C:19]3[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=3)[C:22]([OH:24])=[O:23])[C:14]=2[S:15][CH2:16][CH2:17][CH3:18])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57857096Methyl 3-[4-(cyclohexylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoate

Product 1

HCID 595160843-[4-(Cyclohexylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-[4-(cyclohexylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoate (175 mg, 0.45), (Intermediate #12) was dissolved in methanol (10 mL), treated with 2M aqueous sodium hydroxide solution (1.125 mL) and stirred at ambient temperature for 18 h. Methanol was removed by evaporation under reduced pressure and the clear solution diluted with water (25 ml). 2M HCl was added to pH4 and the mixture extracted with ethyl acetate (2×25 mL). The combined extracts were washed with water (2×10 mL) and brine (10 mL), dried (MgSO4) and evaporated to give the title product as a white solid. (115 mg, 65%)

Workup

  1. customMethanol was removed by evaporation under reduced pressure
  2. additionthe clear solution diluted with water (25 ml)
  3. addition2M HCl was added to pH4
  4. extractionthe mixture extracted with ethyl acetate (2×25 mL)
  5. washThe combined extracts were washed with water (2×10 mL) and brine (10 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-b1da1f2e49e043848ec133376df55ceb
Source dataset
uspto-grants-2013_01
Patent number
US08344016B2

Reaction notes

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