Sodium Hydroxide → HCID 49779125, compound

HRID 386383Notes

Reaction equation

HRID 386383 reaction equation
[CH3:1][C:2]([S:9][C:10]1[N: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)[N:13]=[CH:12][CH:11]=1)([CH3:8])[C:3]([O:5]CC)=[O:4].[OH-].[Na+]>CO>[CH3:8][C:2]([S:9][C:10]1[N: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)[N:13]=[CH:12][CH:11]=1)([CH3:1])[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66820792HCID 66820792, compound

Product 1

HCID 49779125HCID 49779125, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 2-methyl-2-(1-(naphthalen-1-yl)-1H-pyrazol-5-ylthio)propanoate (124 mg, 0.36 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 temperature and the methanol removed. Water was added, neutralized with 1N HCl 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 2-methyl-2-(1-(naphthalen-1-yl)-1H-pyrazol-5-ylthio)propanoic acid as a solid.

Workup

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

Sources & evidence

ORD record
ord-dd4379edbde8414ca4b428ec7545fb05
Source dataset
uspto-grants-2013_02
Patent number
US08372807B2

Reaction notes

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