Benzyl chloroformate → (R)-3-((Benzyloxy)carbonyl)thiazolidine-4-carboxylic acid

Participants

Reaction Steps

To a solution of 2.66 g of (R)-(-)-thiazolidine-4-carboxylic acid in 10 ml of a 2N-aqueous sodium hydroxide solution were added 4.1 g of benzyloxycarbonyl chloride and 15 ml of a 2N-aqueous sodium hydroxide solution with stirring under ice-cooling at the same time, and then the mixture was stirred for 2 hours at room temperature. The reaction mixture was washed with diethyl ether. The reaction mixture was then acidified by adding hydrochloric acid under ice-cooling. The mixture was allowed to stand for 30 minutes, and then the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to obtain 4.14 g of (R)-(-)-3-benzyloxycarbonylthiazolidine-4-carboxylic acid as a colorless clear viscous oil. The oily substance was allowed to stand under cooling to form a solid, and the solid was recrystallized from diethyl ether-petroleum ether to obtain a pure (R)-(-)-3-benzyloxycarbonylthiazolidine-4-carboxylic acid.

Provenance & Evidence