Water → 3-{[Isobutyl(methyl)amino]methyl}-5-methylbenzoic acid

HRID 14134

Reaction equation

HRID 14134 reaction equation
[CH2:1]([N:5]([CH2:7][C:8]1[CH:9]=[C:10]([CH:15]=[C:16]([CH3:18])[CH:17]=1)[C:11]([O:13]C)=[O:12])[CH3:6])[CH:2]([CH3:4])[CH3:3].O.[OH-].[Li+]>CO.O1CCCC1>[CH2:1]([N:5]([CH2:7][C:8]1[CH:9]=[C:10]([CH:15]=[C:16]([CH3:18])[CH:17]=1)[C:11]([OH:13])=[O:12])[CH3:6])[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 21086186Methyl 3-{[isobutyl(methyl)amino]methyl}-5-methylbenzoate

Product 1

HCID 210858333-{[Isobutyl(methyl)amino]methyl}-5-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 3-{[isobutyl(methyl)amino]methyl}-5-methylbenzoate (120 mg, 0.48 mmol) in methanol (2 mL), tetrahydrofuran (1 mL), and water (1 mL) is added lithium hydroxide (200 mg, 4.8 mmol), and the reaction mixture stirred at room temperature for 2 h. The reaction mixture is concentrated under reduced pressure, dissolved in methylene chloride, filtered, and the filtrate concentrated under reduced pressure to provide the title compound. ESI MS m/z 236 [M+H]+.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. dissolutiondissolved in methylene chloride
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-65e577380f604070a60f53b53a12c787
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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