Triethylamine → benzyl N-(E)-[1-oxo-2-(acetylthiomethyl)-3-phenylpropenyl]-beta-alaninate

Participants

Reaction Steps

0.95 g (4 mmol) of (E)-2-acetylthiomethyl-3-phenylpropenoic acid dissolved in 15 ml of anhydrous THF is placed in a round-bottomed flask fitted with a calcium chloride guard tube. The flask is cooled to approximately 0°-5° C. in an ice bath and 1.10 g (4 mmol) of benzyl β-alaninate methanesulphonate and 0.41 g (4 mmol) of triethylamine in 5 ml of chloroform, a solution of 0.54 g (4 mmol) of hydroxybenzotriazole monohydrate in 5 ml of THF and a solution of 0.83 g (4 mmol) of dicyclohexylcarbodiimide in 5 ml of chloroform are successively added with stirring. The mixture is allowed to return to room temperature and is stirred for 6 hours.

Provenance & Evidence