Sodium Hydroxide → HCID 49820406, compound

HRID 386387Notes

Reaction equation

HRID 386387 reaction equation
[CH3:1][C:2]([O:9][C:10]1[C:14]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)=[C:13]([CH3:25])[NH:12][N:11]=1)([CH3:8])[C:3]([O:5]CC)=[O:4].[OH-].[Na+]>CO>[CH3:8][C:2]([O:9][C:10]1[C:14]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)=[C:13]([CH3:25])[NH:12][N:11]=1)([CH3:1])[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 49820405HCID 49820405, compound

Product 1

HCID 49820406HCID 49820406, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 2-methyl-2-(5-methyl-4-(naphthalen-1-yl)-1H-pyrazol-3-yloxy)propanoate (60 mg, 0.18 mmol), aqueous sodium hydroxide solution (10%, 5 mL) and methanol (5 mL) was stirred at reflux for 2 hours. The reaction was then cooled to room and the methanol removed. Water was added, neutralized with aqueous HCl solution (1N) and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated. Purification by preparative thin layer chromatography (95% dichloromethane/5% methanol) afforded compound 2-methyl-2-(5-methyl-4-(naphthalen-1-yl)-1H-pyrazol-3-yloxy)propanoic acid as a solid (40 mg, 71%).

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureThe reaction was then cooled to room
  3. customthe methanol removed
  4. additionWater was added
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated
  8. customPurification by preparative thin layer chromatography (95% dichloromethane/5% methanol)

Sources & evidence

ORD record
ord-88fca877e170488a908aa3eab6d5766b
Source dataset
uspto-grants-2013_02
Patent number
US08372807B2

Reaction notes

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