2-Oxopropanoyl chloride → Pyruvyl-glycine benzyl ester

HRID 2259251Notes

Reaction equation

HRID 2259251 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]=1

Participants

3

Reactant 2

HCID 5217912-Oxopropanoyl chlorideHCID 11701227Benzyl 2-aminoacetate hydrochloride

Product 1

HCID 19003235Pyruvyl-glycine benzyl esterYield 85%

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-3b7fc18920d345b1aa7fb4c70f2ab33c
Source dataset
uspto-grants-1995_12
Patent number
US05472980

Reaction notes

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