Water → Gamma-glutamyl-valyl-glycine

HRID 1484007Notes

Reaction equation

HRID 1484007 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:26]([O:28]CC1C=CC=CC=1)=[O:27])[CH2:3][CH2:4][C:5]([NH:7][C@H:8]([C:12]([NH:14][CH2:15][C:16]([O:18]CC1C=CC=CC=1)=[O:17])=[O:13])[CH:9]([CH3:11])[CH3:10])=[O:6].O>C(O)C.[Pd]>[NH2:1][C@H:2]([C:26]([OH:28])=[O:27])[CH2:3][CH2:4][C:5]([NH:7][C@H:8]([C:12]([NH:14][CH2:15][C:16]([OH:18])=[O:17])=[O:13])[CH:9]([CH3:11])[CH3:10])=[O:6]

Participants

5

Reactant 2

HCID 962WaterHCID 131729420Z-Glu(Val-Gly-OBzl)-OBzl

Product 1

HCID 25099093Gamma-glutamyl-valyl-glycineYield 93.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Z-Glu(Val-Gly-OBzl)-OBzl (6.20 g, 10.03 mmol) described above was suspended in ethanol (200 ml), 10% palladium on carbon (1.50 g) was added to the suspension, and a reduction reaction was performed under a hydrogen atmosphere at 55° C. for 5 hours. During the reaction, 100 ml in a total volume of water was gradually added. The catalyst was removed by filtration using a Kiriyama funnel, and the filtrate was concentrated under reduced pressure to a half volume. The reaction solution was further filtered through a membrane filter, and the filtrate was concentrated under reduced pressure. The residue was dissolved in a small volume of water, and to the solution, ethanol was added to precipitate a crystal, and the crystal was collected by filtration and dried under reduced pressure to obtain γ-Glu-Val-Gly as a white powder (2.85 g, 9.40 mmol).

Workup

  1. customa reduction reaction
  2. additionwas gradually added
  3. customThe catalyst was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure to a half volume
  5. filtrationThe reaction solution was further filtered through a membrane
  6. filtrationfilter
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. dissolutionThe residue was dissolved in a small volume of water
  9. additionto the solution, ethanol was added
  10. customto precipitate a crystal
  11. filtrationthe crystal was collected by filtration
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-93d193000dba44018fa7884efc486810
Source dataset
uspto-grants-2016_08
Patent number
US09420813B2

Reaction notes

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