Water → 2-Methyl-2-(3-pyridyl)thiazolidine-4-carboxylic acid

HRID 129726

Reaction equation

HRID 129726 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)(=O)[CH3:2].[NH2:10][C@H:11]([C:14]([OH:16])=[O:15])[CH2:12][SH:13].O>C(O)C>[CH3:2][C:1]1([C:4]2[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:10][CH:11]([C:14]([OH:16])=[O:15])[CH2:12][S:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 5862L-(+)-CysteineHCID 95893-Acetylpyridine

Product 1

HCID 148815392-Methyl-2-(3-pyridyl)thiazolidine-4-carboxylic acidYield 37.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.63 g of 3-acetylpyridine, 3.63 g of L-cysteine, 25 ml of water and 25 ml of ethanol was refluxed for 24 hours. The reaction mixture was concentrated under reduced pressure, isopropanol was added to the residue, and the resultant powder was collected by filtration. Ethanol was added to the powder, the insoluble matter was filtered off, and the filtrate was concentrated to dryness. The residue was dissolved in water and adjusted to pH 6 by addition of diluted hydrochloric acid under ice cooling and stirring, and the resultant powder was collected by filtration, washed with ethanol and dried to give 2.54 g of 2-methyl-2-(3-pyridyl)thiazolidine-4- carboxylic acid.

Workup

  1. temperaturewas refluxed for 24 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure, isopropanol
  3. additionwas added to the residue
  4. filtrationthe resultant powder was collected by filtration
  5. additionEthanol was added to the powder
  6. filtrationthe insoluble matter was filtered off
  7. concentrationthe filtrate was concentrated to dryness
  8. dissolutionThe residue was dissolved in water
  9. additionadjusted to pH 6 by addition of diluted hydrochloric acid under ice cooling
  10. filtrationthe resultant powder was collected by filtration
  11. washwashed with ethanol
  12. customdried

Sources & evidence

ORD record
ord-d9856abc93b2451cbf7466012acd1937
Source dataset
uspto-grants-1995_11
Patent number
US05470851

Linked notes

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