Benzyl glycinate → Pyruvyl-glycine benzyl ester
Reaction equation
[C:1](Cl)(=[O:5])[C:2]([CH3:4])=[O:3].[CH2:7]([O:14][C:15](=[O:18])[CH2:16][NH2:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[CH2:7]([O:14][C:15](=[O:18])[CH2:16][NH:17][C:1](=[O:5])[C:2]([CH3:4])=[O:3])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1Participants
Procedure
More preferably the thionyl chloride or oxalyl chloride is added to a mechanically stirred suspension of sodium pyruvate in dichloromethane whereby a gas is evolved and pyruvyl chloride is yielded. The pyruvyl chloride is cooled during the dropwise addition of glycine benzyl ester solution to yield pyruvyl-glycine benzyl ester following the warming to room temperature, the addition of water, separation, washing with diluted hydrochloric acid and brine, drying with magnesium sulfate, evaporation of the dichloromethane, precipitation, filtering and drying again. The pyruvyl-glycine benzyl ester is then charged in a hydrogen pressure vessel with ethyl acetate and 4% to 20% palladium on carbon, with the hydrogen pressure being approximately 40-150 psi, such that hydrogen is digested whereby following warming, filtering, concentration, precipitation, filtering and drying there is yielded pyruvyl-glycine.
Sources & evidence
- ORD record
- ord-853d0bfcf69b46e39ed3e4f2831488f6
- Source dataset
- uspto-grants-1994_05
- Patent number
- US05312985
Reaction notes
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