Dichloromethane → HCID 68506411, compound

Participants

Reaction Steps

A solution of DMAP (9.77 g), TEA (55.23 ml) and N,N′-diisopropylcarbodiimide (49.01 ml) in DCM is treated with 5-methyl-isoxazole-3-ylamine (28.8 g) and Boc-β-Ala-OH (50 g) and stirred at room temperature for 18 h. The resulting mixture is diluted with DCM (1750 ml) and washed with 10% citric acid (2×500 ml), saturated sodium hydrogen carbonate solution (2×500 ml), and brine (600 ml). The organic portion is dired (MgSO4), concentrated in vacuo and the crude residue is stirred with iso-hexane (750 ml) for 1 hr. The resulting solid is dissolved in dioxane (400 ml) and treated with 4M HCl in dioxane (350 ml). After 1 hr the precipitate is filtered off and washed with dioxane (100 ml) to afford the 3-amino-N-(5-methyl-isoxazol-3-yl)-propionamide hydrochloride. (MH+ 169.84)

Provenance & Evidence