Water → Gamma-glutamyl-valyl-glycine

HRID 424604Notes

Reaction equation

HRID 424604 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

Then, Z-Glu(Val-Gly-OBzl)-OBzl (6.20 g, 10.03 mmol) was suspended in ethanol (200 ml), and 10% palladium/carbon (1.50 g) was added. A reduction reaction was performed at 55° C. for 5 hours under a hydrogen atmosphere. During the reaction, a total amount of 100 ml 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 mixture 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 ethanol was added to deposit crystals, and the crystals were collected by filtration, and dried under reduced pressure to obtain a white powder of γ-Glu-Val-Gly (2.85 g, 9.40 mmol).

Workup

  1. customA reduction reaction
  2. customDuring the reaction
  3. customThe catalyst was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure to a half volume
  5. filtrationThe reaction mixture 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, and ethanol
  9. additionwas added to deposit crystals
  10. filtrationthe crystals were collected by filtration
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-cd72793410384083b8cf7bb3f77bee84
Source dataset
uspto-grants-2012_01
Patent number
US08106020B2

Reaction notes

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