Pyruvic Acid → 2-Methyl-2,4-thiazolidinedicarboxylic acid

HRID 1503164Notes

Reaction equation

HRID 1503164 reaction equation
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][SH:4].[C:8]([OH:13])(=[O:12])[C:9]([CH3:11])=O>C(O)C>[CH3:11][C:9]1([C:8]([OH:13])=[O:12])[NH:1][CH:2]([C:5]([OH:7])=[O:6])[CH2:3][S:4]1

Participants

4

Reactant 2

HCID 1060Pyruvic AcidHCID 5862L-(+)-Cysteine

Product 1

HCID 983422-Methyl-2,4-thiazolidinedicarboxylic acidYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under an argon atmosphere, L-cysteine (15 g) was dissolved in dry ethanol (35 mL), pyruvic acid (18.6 mL) was added thereto at room temperature, and the mixture was stirred for 3 hours. The resulting solid was collected by filtration under reduced pressure, and washed with ice-cooled ethanol to give 2-methylthiazolidine-2,4-dicarboxylic acid (diastereomer mixture) (23 g, yield 97%).

Workup

  1. filtrationThe resulting solid was collected by filtration under reduced pressure
  2. washwashed with ice-
  3. temperaturecooled ethanol

Sources & evidence

ORD record
ord-a7626b3f9b994fc48dd73fdd84dda01c
Source dataset
uspto-grants-2015_12
Patent number
US09212154B2

Reaction notes

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