Lithium Hydroxide → 3-Benzamido-2-methylbutanoic acid

HRID 1888120Notes

Reaction equation

HRID 1888120 reaction equation
[C:1]([NH:9][CH:10]([CH3:18])[CH:11]([CH3:17])[C:12]([O:14]CC)=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+]>CO.O>[C:1]([NH:9][CH:10]([CH3:18])[CH:11]([CH3:17])[C:12]([OH:14])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 5699253-Benzoylamino-2-methyl-butyric acid, ethyl ester

Product 1

HCID 138635073-Benzamido-2-methylbutanoic acidYield 77.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To ethyl 3-benzamido-2-methylbutanoate (0.08 g, 0.321 mmol) in MeOH (2 mL) and water (1.000 mL) was added lithium hydroxide (0.015 g, 0.642 mmol) at RT. Contents heated at 60° C. for 1.5 h. The reaction mixture was concentrated and partitioned between dichloromethane (10 mL) and 1N HCl (5 mL). The dichloromethane layer is washed with brine (10 mL), dried overt sodium sulfate and concentrated to yield the title compound (0.055 g, 0.249 mmol, 77% yield) as a foamy solid, which was used as such for the subsequent step without further purification. MS (ESI) m/z 222.16 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between dichloromethane (10 mL) and 1N HCl (5 mL)
  3. washThe dichloromethane layer is washed with brine (10 mL)
  4. dry with materialdried overt sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-93d1b7c6472b4c52b8e3fc147484636f
Source dataset
uspto-grants-2013_08
Patent number
US08501782B2

Reaction notes

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