Sulfuric Acid → Leucic acid, L-

HRID 1647136Notes

Reaction equation

HRID 1647136 reaction equation
N[C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].S(=O)(=O)(O)[OH:11].[N+]([O-])([O-])=O.[Na+].[Cl-].[Na+]>O>[OH:11][C@@H:2]([CH2:3][CH:4]([CH3:6])[CH3:5])[C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 6106L-LeucineHCID 24268Sodium Nitrate

Product 1

HCID 83697Leucic acid, L-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

L-Leu-OH (10.0 g) was dissolved in water (150 ml) containing concentrated sulfuric acid (3.2 ml) at 0° C. To the solution was added dropwise a solution of sodium nitrate (7.9 g) in water (50 ml) over 1 hour. The mixture was saturated with sodium chloride and extracted with ethyl acetate (500 ml). The organic layer was dried over magnesium sulfate and concentrated in vacuo. The residual solid was triturated with hexane to give (2S)-2-hydroxy-4-methylvaleric acid (6.51 g).

Workup

  1. extractionextracted with ethyl acetate (500 ml)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residual solid was triturated with hexane

Sources & evidence

ORD record
ord-1c68ac9476074b5a986afae045af642b
Source dataset
uspto-grants-1995_07
Patent number
US05430022

Reaction notes

Loading…