Hydrochloric Acid → Tosyl-L-asparagine

Participants

Reaction Steps

L-Asparagine (10.0 g, 75.7 mmol) was placed in a 500 mL round bottom flask equipped with a magnetic stir bar and an addition funnel. 1N Sodium hydroxide (170 mL, 166.5 mmol) was added along with 50 mL dioxane. p-Toluenesulfonyl chloride (15.88 g, 83.27 mmol) dissolved in dioxane (50 mL) was added to the reaction mixture with vigorous stirring. The reaction mixture was then stirred for 2 h at room temperature, cooled to 0° C., and acidified to pH 2-3 with hydrochloric acid (conc.). The desired product 14-2 formed as a white crystalline solid (20.3 g, 94%) that was collected by filtration.

Provenance & Evidence