Ethanol → Glutamyl-norvaline

HRID 44152Notes

Reaction equation

HRID 44152 reaction equation
C(O)C.[NH:4](C(OCC1C=CC=CC=1)=O)[C@H:5]([C:25]([O:27]CC1C=CC=CC=1)=[O:26])[CH2:6][CH2:7][C:8]([NH:10][C@H:11]([C:15]([O:17]CC1C=CC=CC=1)=[O:16])[CH2:12][CH2:13][CH3:14])=[O:9].[H][H]>[Pd].O>[NH2:4][C@H:5]([C:25]([OH:27])=[O:26])[CH2:6][CH2:7][C:8]([NH:10][C@H:11]([C:15]([OH:17])=[O:16])[CH2:12][CH2:13][CH3:14])=[O:9]

Participants

6

Reactant 3

HCID 702EthanolHCID 131730876Z-Glu(Nva-OBzl)-OBzlHCID 178418361HCID 178418361, compound

Product 1

HCID 87349698Glutamyl-norvalineYield 71.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent2×

Procedure

To a mixed solution of ethanol (150 mL) and water (30 mL), Z-Glu(Nva-OBzl)-OBzl (4.05 g) and 5% palladium on carbon (5% palladium/carbon, 0.70 g) was added, and a catalytic reducing reaction was carried out at 50° C. overnight (14 hours) in a hydrogen gas atmosphere. Water (50 mL) was added to the reaction system in small portions during the reaction. The palladium/carbon was removed from the reaction system through filtration and the resulting filtrate was concentrated under reduced pressure. The residue was recrystallized from a small amount of water and ethanol to thus give γ-Glu-Nva (1.50 g) as white crystals. Furthermore, the crystals were dissolved in water (100 mL) followed by the lyophilization of the solution to give γ-Glu-Nva (1.27 g, 5.16 mM) as white powder. The characteristic values thereof are given below:

Workup

  1. customreaction
  2. custom(14 hours)
  3. customThe palladium/carbon was removed from the reaction system through filtration
  4. concentrationthe resulting filtrate was concentrated under reduced pressure
  5. customThe residue was recrystallized from a small amount of water and ethanol to thus give γ-Glu-Nva (1.50 g) as white crystals
  6. dissolutionFurthermore, the crystals were dissolved in water (100 mL)

Sources & evidence

ORD record
ord-6fd17569bc62485fae8e75a4329bbbfc
Source dataset
uspto-grants-2013_09
Patent number
US08541379B2

Reaction notes

Loading…