Ethanol → gamma-Glu-Nle

HRID 44154Notes

Reaction equation

HRID 44154 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:23]([O:25]CC1C=CC=CC=1)=[O:24])[CH2:3][CH2:4][C:5]([NH:7][C@H:8]([C:13]([O:15]CC1C=CC=CC=1)=[O:14])[CH2:9][CH2:10][CH2:11][CH3:12])=[O:6].C(O)C.[H][H]>[Pd].O>[NH2:1][C@H:2]([C:23]([OH:25])=[O:24])[CH2:3][CH2:4][C:5]([NH:7][C@H:8]([C:13]([OH:15])=[O:14])[CH2:9][CH2:10][CH2:11][CH3:12])=[O:6]

Participants

6

Reactant 3

HCID 702EthanolHCID 131730877Z-Glu(Nle-OBzl)-OBzlHCID 178418361HCID 178418361, compound

Product 1

HCID 89106960gamma-Glu-NleYield 7.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent2×

Procedure

Z-Glu(Nle-OBzl)-OBzl (4.05 g) and 5% palladium on carbon (5% palladium/carbon, 0.40 g) were added to a mixed solution of ethanol (50 mL) and water (10 mL), and a catalytic reducing reaction was carried out at 50° C. overnight (14 hours) in a hydrogen gas atmosphere. Water (10 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-Nle (0.29 g) as hygroscopic crystals. Furthermore, the crystals were dissolved in water (30 mL) followed by the lyophilization of the solution to give γ-Glu-Nle (0.13 g, 0.50 mM) as a white powder. The characteristic values thereof will be 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-Nle (0.29 g) as hygroscopic crystals
  6. dissolutionFurthermore, the crystals were dissolved in water (30 mL)

Sources & evidence

ORD record
ord-f8a8d454a9f3469e932607f80bfd0d7e
Source dataset
uspto-grants-2013_09
Patent number
US08541379B2

Reaction notes

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