Benzylamine → (2R,4R)-2-amino-4-benzyl-4-hydroxyglutaric acid

HRID 2244792

Reaktionsgleichung

Reaktionsgleichung von HRID 2244792
[CH2:1]([C:8]([OH:18])([C:15]([OH:17])=[O:16])[CH2:9][C:10](=O)[C:11]([OH:13])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([NH2:26])C1C=CC=CC=1>CO.[C].[Pd]>[NH2:26][C@H:10]([CH2:9][C@@:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([OH:18])[C:15]([OH:17])=[O:16])[C:11]([OH:13])=[O:12].[NH2:26][C@@H:10]([CH2:9][C@@:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([OH:18])[C:15]([OH:17])=[O:16])[C:11]([OH:13])=[O:12]

Komponenten

6

Edukt 2

HCID 7504BenzylamineHCID 101714744-Benzyl-4-hydroxy-2-ketoglutaric acid

Produkt 2

HCID 10354897(2R,4R)-2-amino-4-benzyl-4-hydroxyglutaric acidHCID 86595816(2S,4R)-2-amino-4-benzyl-4-hydroxyglutaric acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

0.13 g (0.52 mmol) of 4-benzyl-4-hydroxy-2-ketoglutaric acid and 0.11 ml (1.0 mmol) of benzylamine were dissolved in 5 ml of methanol, to which 0.1 g of 5% palladium carbon (50% hydrous product) was added, for reaction under hydrogen atmosphere at ambient temperature and atmospheric pressure. Two days later, the catalyst was filtered off, and the reaction solution was concentrated to dryness, to obtain 0.03 g (0.12 mmol) of (2S,4S)/(2R,4R)-2-amino-4-benzyl-4-hydroxyglutaric acid and 0.06 g (0.24 mmol) of (2R,4S)/(2S,4R)-2-amino-4-benzyl-4-hydroxyglutaric acid as a mixture.

Aufarbeitung

  1. additionwas added, for reaction under hydrogen atmosphere at ambient temperature
  2. filtrationTwo days later, the catalyst was filtered off
  3. concentrationthe reaction solution was concentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-599128d384fe4de79c241d7d51b9677d
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07678925B2

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