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

HRID 1464367

Reaktionsgleichung

Reaktionsgleichung von HRID 1464367
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]

Komponenten

5

Edukt 2

HCID 439524D-LeucineHCID 23668193Sodium Nitrite

Produkt 1

HCID 439960(R)-2-hydroxy-4-methylpentanoic acidAusbeute 41,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-69c19abdbb464d54854f17c34badf796
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05304549

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