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

HRID 133671

Reaction equation

HRID 133671 reaction equation
[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]

Participants

6

Reactant 2

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

Product 2

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

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-650ba3a6236049d4823e53568020ca00
Source dataset
uspto-grants-2008_06
Patent number
US07390909B2

Linked notes

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