L-Phenylalanine → 3-Phenyllactic acid, (S)-

HRID 10917

Reaktionsgleichung

Reaktionsgleichung von HRID 10917
N([O-])=[O:2].[Na+].N[C@H:6]([C:14]([OH:16])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O.S(=O)(=O)(O)O>[OH:2][C@@H:6]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]([OH:16])=[O:15]

Komponenten

5

Edukt 2

HCID 6140L-PhenylalanineHCID 23668193Sodium Nitrite

Produkt 1

HCID 4447183-Phenyllactic acid, (S)-Ausbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

A solution of 14 g (217 mmol) of sodium nitrite in 20 ml of water was added dropwise to a solution of 14 g (85 mmol) of L-phenylalanine in 100 ml of 1 N sulfuric acid at 0° C. over 3 hours, and the mixture was stirred overnight at room temperature. After extraction with three 100-ml portions of ethyl acetate, the organic phase was dried over sodium sulfate. The optical purity of (2S)-2-hydroxy-3-phenylpropionic acid in this extract was 93.0% ee. The solvent was distilled off under reduced pressure to give 12 g of crude (2S)-2-hydroxy-3-phenylpropionic acid. Further, this crude product was purified by recrystallization using 35 ml of ethyl acetate to give 7.5 g (yield 53%) of the desired (2S)-2-hydroxy-3-phenylpropionic acid. The proton concentration (normality) in the reaction of this comparative example was 1.0 mol/kg, the amount of the protonic acid was 1.2 equivalents (relative to L-phenylalanine), and the reaction temperature was 0° C. to room temperature.

Aufarbeitung

  1. extractionAfter extraction with three 100-ml portions of ethyl acetate
  2. dry with materialthe organic phase was dried over sodium sulfate
  3. distillationThe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-96950af56707463597c262dab0ced699
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094926B2

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