L-(+)-Cysteine → 2-(3-Piridyl)thiazolidine-4-carboxylic acid

HRID 892799Notes

Reaction equation

HRID 892799 reaction equation
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][SH:4].[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]=O)[CH:9]=1>C(O)C>[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]2[NH:1][CH:2]([C:5]([OH:7])=[O:6])[CH2:3][S:4]2)[CH:9]=1

Participants

4

Reactant 2

HCID 5862L-(+)-CysteineHCID 103713-Pyridinecarboxaldehyde

Product 1

HCID 3275932-(3-Piridyl)thiazolidine-4-carboxylic acidYield 80,855%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

Cysteine (24.2 g, 0.2 mole) and 3-pyridine carboxaldehyde (21.4 g, 0.2 mmole) were suspended in 60% aqueous ethanol (400 mL) and the mixture was heated at 100° C. for 5 hours. The reaction mixture was then cooled and most of the solvent was removed in vacuo. The resulting slurry was washed with ethanol and filtered. This material was dried overnight in vacuo at 50° C. to afford the thiazolidine acid (34 g, 81%).

Workup

  1. temperatureThe reaction mixture was then cooled and most of the solvent
  2. customwas removed in vacuo
  3. washThe resulting slurry was washed with ethanol
  4. filtrationfiltered
  5. customThis material was dried overnight in vacuo at 50° C.

Sources & evidence

ORD record
ord-483e5aa794964bf7a81c912380198b5b
Source dataset
uspto-grants-1992_06
Patent number
US05120751

Reaction notes

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