L-(+)-Cysteine → 2-Methylthiazolidine-2,4-dicarboxylic acid 2-ethyl ester

HRID 1503165Notes

Reaction equation

HRID 1503165 reaction equation
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][SH:4].[C:8]([O:13][CH2:14][CH3:15])(=[O:12])[C:9]([CH3:11])=O>O.C(O)C>[CH3:15][CH2:14][O:13][C:8]([C:9]1([CH3:11])[NH:1][CH:2]([C:5]([OH:7])=[O:6])[CH2:3][S:4]1)=[O:12]

Participants

5

Reactant 2

HCID 5862L-(+)-CysteineHCID 12041Ethyl pyruvate

Product 1

HCID 866809292-Methylthiazolidine-2,4-dicarboxylic acid 2-ethyl esterYield 70%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Under an argon atmosphere, L-cysteine (10 g) was dissolved in pure water (150 ml), and ethyl pyruvate (19.7 ml) dissolved in ethanol (10 ml) at room temperature was gradually added to the solution. The mixture was stirred overnight at room temperature, and concentrated under reduced pressure. The obtained solid was dissolved in pure water, and the solution was extracted with chloroform. The extract was dried over magnesium sulfate, and concentrated under reduced pressure to give an oil. The oil was recrystallized from chloroform/hexane to give 2-methylthiazolidine-2,4-dicarboxylic acid 2-ethyl ester (diastereomer mixture) (12.7 g, yield 70%).

Workup

  1. additionwas gradually added to the solution
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe obtained solid was dissolved in pure water
  4. extractionthe solution was extracted with chloroform
  5. dry with materialThe extract was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give an oil
  8. customThe oil was recrystallized from chloroform/hexane

Sources & evidence

ORD record
ord-68684edfb80145f98519751caedce913
Source dataset
uspto-grants-2015_12
Patent number
US09212154B2

Reaction notes

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