Sodium Hydroxide → HCID 25254293, compound

HRID 333777Notes

Reaction equation

HRID 333777 reaction equation
C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([CH:11]([CH3:25])[C:12]([OH:24])([C:17]2[CH:22]=[N:21][CH:20]=[C:19]([CH3:23])[N:18]=2)[C:13]([F:16])([F:15])[F:14])[CH:5]=1.[OH-].[Na+]>CO>[Cl:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:26])=[O:2])=[CH:5][C:6]=1[CH:11]([CH3:25])[C:12]([OH:24])([C:17]1[CH:22]=[N:21][CH:20]=[C:19]([CH3:23])[N:18]=1)[C:13]([F:16])([F:14])[F:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57421262HCID 57421262, compound

Product 1

HCID 25254293HCID 25254293, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 4-chloro-3-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(6-methyl-pyrazin-2-yl)-propyl]-benzoic acid methyl ester (50 mg) in methanol (1 mL) was added an aqueous solution of 1N NaOH (0.257 mL) and the mixture was allowed to stir at 40° C. for 12 hours. Methanol was removed by evaporation and the residue was diluted with water. The solution was extracted with ethyl acetate and the organic layer was washed with water. The aqueous layers were combined and aqueous HCl (1N, 0.257 mL) was added. The solution was extracted with ethyl acetate twice and the organic layers were washed with brine, dried over MgSO4 and evaporated. The residue was evaporated once from heptane to give, after drying, the title compound as a white solid (47 mg). MS (m/e, ISP neg. ion): 373.1 (M−H+)−.

Workup

  1. customMethanol was removed by evaporation
  2. additionthe residue was diluted with water
  3. extractionThe solution was extracted with ethyl acetate
  4. washthe organic layer was washed with water
  5. additionaqueous HCl (1N, 0.257 mL) was added
  6. extractionThe solution was extracted with ethyl acetate twice
  7. washthe organic layers were washed with brine
  8. dry with materialdried over MgSO4
  9. customevaporated
  10. customThe residue was evaporated once from heptane
  11. customto give
  12. customafter drying

Sources & evidence

ORD record
ord-248942f1c82143efb35217d3c15a49d9
Source dataset
uspto-grants-2014_11
Patent number
US08883786B2

Reaction notes

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