Sodium Hydroxide → HCID 25005937, compound

HRID 1799364Notes

Reaction equation

HRID 1799364 reaction equation
[CH2:1]([S:4][C:5]1[N:9]([C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[CH:12][CH:11]=2)[N:8]=[CH:7][C:6]=1[C:20]([N:22]1[CH2:26][CH2:25][CH:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]([F:36])([F:35])[F:34])[CH2:23]1)=[O:21])[CH2:2][CH3:3].[OH-].[Na+]>CO>[CH2:1]([S:4][C:5]1[N:9]([C:10]2[CH:11]=[CH:12][C:13]([C:14]([OH:16])=[O:15])=[CH:18][CH:19]=2)[N:8]=[CH:7][C:6]=1[C:20]([N:22]1[CH2:26][CH2:25][CH:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]([F:34])([F:35])[F:36])[CH2:23]1)=[O:21])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59516100HCID 59516100, compound2×

Product 1

HCID 25005937HCID 25005937, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-[5-propylsulfanyl-4-[3-[2-(trifluoromethyl)phenyl]pyrrolidine-1-carbonyl]pyrazol-1-yl]benzoate (Intermediate #6) (177 mg, 0.34 mmol) was stirred at ambient temperature for 18 h in a mixture of methanol (5 mL) and 2M sodium hydroxide (0.855 mL, 1.71 mmol) for 18 h. The reaction mixture was evaporated to remove the methanol. The residue was dissolved in water (20 mL) and acidified to pH4 with 2M HCl. The resulting white precipitate was recovered by filtration, washed with water and dried under vacuum to give the title compound as a white solid (116 mg, 68%).

Workup

  1. customThe reaction mixture was evaporated
  2. customto remove the methanol
  3. dissolutionThe residue was dissolved in water (20 mL)
  4. filtrationThe resulting white precipitate was recovered by filtration
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-384bb9e7ee194b5982be63dfc8795667
Source dataset
uspto-grants-2013_01
Patent number
US08344016B2

Reaction notes

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