D-Leucine → (R)-2-hydroxy-4-methylpentanoic acid

HRID 1464367

Reaction equation

HRID 1464367 reaction equation
N[C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].N([O-])=[O:11].[Na+]>O.S(=O)(=O)(O)O>[C:7]([OH:9])(=[O:8])[C@@H:2]([CH2:3][CH:4]([CH3:6])[CH3:5])[OH:11]

Participants

5

Reactant 2

HCID 439524D-LeucineHCID 23668193Sodium Nitrite

Product 1

HCID 439960(R)-2-hydroxy-4-methylpentanoic acidYield 41.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

400 g of D-leucine was dissolved in 5 l of water containing 296 ml of concentrated sulfuric acid and cooled to -2°. A solution of 421 g of sodium nitrite in 1.25 l of water was added slowly while holding the temperature at -2°. The mixture was stirred at 0° for 1.5 hours and then allowed to warm to room temperature overnight. The mixture was extracted three times with ethyl acetate. The combined organic extracts were washed with sodium chloride solution, dried over anhydrous magnesium sulfate and evaporated to give 168 g of D-leucic acid as a pale yellow oil.

Workup

  1. temperaturecooled to -2°
  2. customat -2°
  3. extractionThe mixture was extracted three times with ethyl acetate
  4. washThe combined organic extracts were washed with sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-69c19abdbb464d54854f17c34badf796
Source dataset
uspto-grants-1994_04
Patent number
US05304549

Linked notes

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