Sulfuric Acid → 3-Phenyllactic acid, (S)-

HRID 10918

Reaktionsgleichung

Reaktionsgleichung von HRID 10918
N[C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.S(=O)(=O)(O)[OH:14].N([O-])=O.[Na+]>O>[OH:14][C@@H:2]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:10]([OH:12])=[O:11]

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 6140L-PhenylalanineHCID 23668193Sodium Nitrite

Produkt 1

HCID 4447183-Phenyllactic acid, (S)-Ausbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

L-Phenylalanine (10.00 g, 60.5 mmol) was added to a dilution of 8.88 g (90.5 mmol) of concentrated sulfuric acid in 110 g of water and then, at an inside temperature of 40° C., a mixture of 10.45 g (151.5 mmol) of sodium nitrite and 20 g of water was added over 5 hours. After addition, the mixture was further stirred at 40° C. and, thereafter, the same work-up procedure as in Example 1 was followed. The combined extract (146.9 g) obtained contained 8.9 g of (2S)-2-hydroxy-3-phenylpropionic acid (yield 89%, optical purity 94.3% ee). The proton concentration (normality) in the reaction of this example was 1.7 mol/kg, the amount of the protonic acid was 3.0 equivalents (relative to L-phenylalanine), and the reaction temperature was 40° C.

Aufarbeitung

  1. additionwas added over 5 hours
  2. additionAfter addition
  3. extractionThe combined extract (146.9 g)
  4. customobtained

Quellen und Nachweise

ORD-Eintrag
ord-34b06c52d9884760b076e7e3869bff2c
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094926B2

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