DL-valine → 3-Methyl-2-(phenylformamido)butanoic acid

HRID 1619583Notes

Reaction equation

HRID 1619583 reaction equation
[NH2:1][CH:2]([CH:6]([CH3:8])[CH3:7])[C:3]([OH:5])=[O:4].[OH-].[Na+].[C:11](Cl)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>O>[C:11]([NH:1][CH:2]([CH:6]([CH3:8])[CH3:7])[C:3]([OH:5])=[O:4])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 1182DL-valineHCID 7412Benzoyl chlorideHCID 14798Sodium Hydroxide2×

Product 1

HCID 2266823-Methyl-2-(phenylformamido)butanoic acidYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-amino-3-methylbutanoic acid (500 mg, 4.27 mmol) in 2N NaOH (2.35 ml, 4.69 mmol) was stirred at RT for 30 minutes, then the reaction mixture was cooled at 0° C., and benzoyl chloride (471 μl, 4.05 mmol) and 2N NaOH (2.35 ml, 4.69 mmol) were simultaneously added dropwise from two different syringes. The reaction was stirred at RT for 3 hours. Water was added, the aqueous phase was washed with Et2O, then acidified with 1M HCl and back-extracted with Et2O, dried over Na2SO4 and evaporated. The residue was triturated with i-Pr2O to obtain 2-benzamido-3-methylbutanoic acid (780 mg, 83% yield).

Workup

  1. washthe aqueous phase was washed with Et2O
  2. extractionback-extracted with Et2O
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residue was triturated with i-Pr2O

Sources & evidence

ORD record
ord-e5fb7075340b4c779d9d670de45c69ae
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

Loading…