Sulfuric Acid → Leucic acid, L-

HRID 2256835Notes

Reaction equation

HRID 2256835 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-89a188319d744fac9180e2ed4e24f816
Source dataset
uspto-grants-1997_08
Patent number
US05656604

Reaction notes

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