Pyruvyl-glycine benzyl ester → Pyruvoylglycine

HRID 2259252Notes

Reaction equation

HRID 2259252 reaction equation
C([O:8][C:9](=[O:17])[CH2:10][NH:11][C:12](=[O:16])[C:13]([CH3:15])=[O:14])C1C=CC=CC=1>O>[C:12]([NH:11][CH2:10][C:9]([OH:17])=[O:8])(=[O:16])[C:13]([CH3:15])=[O:14]

Participants

3

Reactant 1

HCID 19003235Pyruvyl-glycine benzyl ester

Product 1

HCID 6451625Pyruvoylglycine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Preferably in this method of synthesis, the thionyl chloride or oxalyl chloride is added to a suspension of sodium pyruvate to yield the pyruvyl chloride to which is added the of glycine benzyl ester hydrochloride. The yield a pyruvyl-glycine benzyl ester. The yielding of the pyruvyl-glycine benzyl ester occurs after warming, the addition of water, separation, washing, drying, evaporation, precipitation, filtering, and drying again. The pyruvyl-glycine benzyl ester is then charged in a hydrogen pressure vessel in a solvent and a palladium on carbon catalyst, with the hydrogen pressure being approximately 60 psi such that hydrogen is digested whereby following filtering, concentration, precipitation, filtering, and drying there is yielded pyruvyl-glycine.

Workup

  1. temperatureafter warming
  2. washwashing
  3. customdrying
  4. customevaporation, precipitation
  5. filtrationfiltering
  6. customdrying again
  7. additionThe pyruvyl-glycine benzyl ester is then charged in a hydrogen pressure vessel in a solvent
  8. filtrationfollowing filtering
  9. concentrationconcentration, precipitation
  10. filtrationfiltering
  11. customdrying there

Sources & evidence

ORD record
ord-04aef4da9df045cab5eb0b2a8be0ec97
Source dataset
uspto-grants-1995_12
Patent number
US05472980

Reaction notes

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