Benzaldehyde → 2-Phenylthiazolidine-4-carboxylic acid methyl ester

HRID 2081505Notes

Reaction equation

HRID 2081505 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][SH:8])[NH2:6].C(=O)([O-])O.[Na+].[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CCOCC>CO>[CH3:2][O:3][C:4]([CH:5]1[CH2:7][S:8][CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH:6]1)=[O:9]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 2733208L-Cysteine, methyl ester, hydrochloride

Product 1

HCID 147909142-Phenylthiazolidine-4-carboxylic acid methyl esterYield 76.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1.72 g of L-cysteine methylester hydrochloride was neutralized by addition of 0.84 g of sodium hydrogen carbonate. The resulting ester was dissolved in 2 ml of methanol, and to this solution was added a solution of 0.94 g of benzaldehyde in 3 ml of methanol. The mixture was then stirred at room temperature for 40 hours under a nitrogen atmosphere. Ether was added to the reaction mixture, and then the mixture was extracted with diluted hydrochloric acid. The extract was neutralized by addition of sodium hydrogen carbonate and then extracted with ether. The organic portion was dried over anhydrous sodium sulfate and placed under reduced pressure for distilling off the solvent. There was obtained 1.51 g of 4-methoxycarbonyl-2-phenylthiazolidine as a colorless oil.

Workup

  1. extractionthe mixture was extracted with diluted hydrochloric acid
  2. additionThe extract was neutralized by addition of sodium hydrogen carbonate
  3. extractionextracted with ether
  4. dry with materialThe organic portion was dried over anhydrous sodium sulfate
  5. distillationfor distilling off the solvent

Sources & evidence

ORD record
ord-554251fd01f6481f822dc717d0d133e5
Source dataset
uspto-grants-1993_02
Patent number
US05183811

Reaction notes

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