L-(+)-Cysteine → 3-Acetyl-2-(2-carboxyphenyl)-4-thiazolidinecarboxylic acid

HRID 1770205Notes

Reaction equation

HRID 1770205 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([OH:3])=[O:2].[NH2:12][C@H:13]([C:16]([OH:18])=[O:17])[CH2:14][SH:15].C([O-])([O-])=O.[K+].[K+].[C:25](OC(=O)C)(=[O:27])[CH3:26]>O.C1COCC1>[C:25]([N:12]1[CH:13]([C:16]([OH:18])=[O:17])[CH2:14][S:15][CH:6]1[C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[C:1]([OH:3])=[O:2])(=[O:27])[CH3:26]

Participants

7

Reactant 4

HCID 5862L-(+)-CysteineHCID 7918Acetic AnhydrideHCID 8406Phthalaldehydic acidHCID 11430Potassium Carbonate

Product 1

HCID 200955393-Acetyl-2-(2-carboxyphenyl)-4-thiazolidinecarboxylic acidYield 22%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 6 of 2-carboxybenzaldehyde and 4.8 g of cysteine in 100 ml of water was stirred for 15 minutes. After adding 10 g of K2CO3, the solution was cooled to 0° C. and a solution of 8 g of acetic anhydride in THF was added. After everything had been added, the solution was stirred for a further 15 minutes at 0° C. and then for 1 hour at room temperature. The solution was concentrated under reduced pressure in order to evaporate THF, acidified to pH 1-2 with sulphuric acid and extracted with ethyl acetate. After drying over MgSO4 and evaporation of the solvent, the residue was crystallised from ethyl acetate/diethyl ether. Yield 22%.

Workup

  1. additionAfter everything had been added
  2. waitfor 1 hour at room temperature
  3. concentrationThe solution was concentrated under reduced pressure in order
  4. customto evaporate THF
  5. extractionextracted with ethyl acetate
  6. dry with materialAfter drying over MgSO4 and evaporation of the solvent
  7. customthe residue was crystallised from ethyl acetate/diethyl ether

Sources & evidence

ORD record
ord-d01dda2c38db46dfbfb4abb5f894c80e
Source dataset
uspto-grants-1995_01
Patent number
US05385922

Reaction notes

Loading…