4-Methoxybenzenesulfonyl chloride → N-[4-methoxybenzenesulfonyl]-(D)-threonine

Participants

Reaction Steps

To a solution of D-threonine (5.0 g, 0.042 mol) in water (50 mL) and dioxane (50 mL) containing triethylamine (8.9 mL, 0.063 mol) at room temperature is added 4-methoxybenzenesulfonyl chloride (9.54 g, 0.046 mol). The reaction mixture is stirred overnight at room temperature. Most of the dioxane is evaporated off, and the pH is adjusted to pH=2 with 1N HCl. The mixture is then extracted with ethyl acetate. The combined organic extracts are washed with brine, dried (Na2SO4), and concentrated in vacuo to provide N-[4-methoxybenzenesulfonyl]-(D)-threonine.

Provenance & Evidence