Sodium Hydroxide → 2-(1-(4-Methoxy-3,5-dimethylphenylamino)cyclobutyl)acetic acid

HRID 2103080Notes

Reaction equation

HRID 2103080 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([NH:10][C:11]2([CH2:15][C:16]([O:18]CC)=[O:17])[CH2:14][CH2:13][CH2:12]2)=[CH:5][C:4]=1[CH3:21].[OH-].[Na+]>CCO>[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([NH:10][C:11]2([CH2:15][C:16]([OH:18])=[O:17])[CH2:14][CH2:13][CH2:12]2)=[CH:5][C:4]=1[CH3:21]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69053175Ethyl 2-(1-(4-methoxy-3,5-dimethylphenylamino)cyclobutyl)acetate

Product 1

HCID 690565892-(1-(4-Methoxy-3,5-dimethylphenylamino)cyclobutyl)acetic acidYield 71.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-(1-(4-methoxy-3,5-dimethylphenylamino)cyclobutyl)acetate (1 g) in EtOH was added an aqueous solution of NaOH (2.5 g). The mixture was stirred at room temperature overnight, concentrated and water was added to the residue. After addition of HCl to adjust the pH 2-3, the solution was then washed with ethyl acetate (3×20 mL). The organic layer was dried over Na2SO4 and the solvent was removed by evaporation to give 2-(1-(4-methoxy-3,5-dimethylphenylamino)-cyclobutyl)acetic acid (650 mg) as a white solid. MS: m/z 264 (100, M+H)+

Workup

  1. concentrationconcentrated
  2. additionwater was added to the residue
  3. additionAfter addition of HCl
  4. washthe solution was then washed with ethyl acetate (3×20 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-2dcedfd4ef2b48f6aa545b9aa2fb91db
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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