N-Benzyloxycarbonyl-valine glycine-methylester → (S)-3-Isopropyl-2,5-piperazinedione

HRID 25849Notes

Reaction equation

HRID 25849 reaction equation
C([O:8][C:9]([NH:11][C@H:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14])=O)C1C=CC=CC=1.COC(=O)[CH2:22][NH2:23]>CO.[Pd]>[CH:13]([C@@H:12]1[NH:11][C:9](=[O:8])[CH2:22][NH:23][C:16]1=[O:18])([CH3:15])[CH3:14]

Participants

4

Reactant 1

HCID 69129945N-Benzyloxycarbonyl-valine glycine-methylester

Product 1

HCID 736942(S)-3-Isopropyl-2,5-piperazinedioneYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 27.14 g (84.19 mmol) N-Benzyloxycarbonyl-valine-glycine-methylester (82) in 600 ml dry methanol was hydrogenated by adding Pd/C-catalyst and stirring the resulting mixture under H2 at r.t. for 4 h. After that the mixture was filtered through celite and the remaining solution was refluxed for 24 h. Evaporation of the solvent yielded 13.17 g (84.33 mmol, 100%) 6-(S)-Isopropyl-piperazine-2,5-dione (83) as a white solid.

Workup

  1. filtrationAfter that the mixture was filtered through celite
  2. temperaturethe remaining solution was refluxed for 24 h
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-1adbe963f52c44e0aa96764270b90336
Source dataset
uspto-grants-2005_02
Patent number
US06858600B2

Reaction notes

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