2-Oxopropanoyl chloride → Pyruvyl-glycine benzyl ester
Reaction equation
[C:1](Cl)(=[O:5])[C:2]([CH3:4])=[O:3].Cl.[CH2:8]([O:15][C:16](=[O:19])[CH2:17][NH2:18])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[CH2:8]([O:15][C:16](=[O:19])[CH2:17][NH:18][C:1](=[O:5])[C:2]([CH3:4])=[O:3])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1Participants
3
Procedure
The improved method of synthesis involves the reaction of sodium pyruvate with thionyl chloride or preferably with oxalyl chloride to form pyruvyl chloride. The pyruvyl chloride is then reacted with glycine benzyl ester hydrochloride to form the pyruvyl-glycine benzyl ester, with a yield of about 85%. The pyruvyl-glycine benzyl ester then undergoes hydrogenolysis to obtain pyruvyl-glycine with a yield of about 90%. It can be readily appreciated that the ultimate yield of pyruvyl-glycine using this improved method is substantially higher than the yield associated with the traditional method of synthesis. This improved method is set forth below.
Sources & evidence
- ORD record
- ord-b94aca0fa80d4ab99fbd2cab1d848940
- Source dataset
- uspto-grants-1993_10
- Patent number
- US05256697
Reaction notes
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