3-Amino-5-methylisoxazole → HCID 22690051, compound

A solution of DMAP (9.77 g, 0.08 mol), TEA (55.23 ml, 0.396 mol) and DCI (49.01 ml, 0.317 mol) in DCM (250 ml) is treated with 5-methyl-isoxazole-3-ylamine (28.8 g, 0.290 mol) and Boc-Beta-Ala-OH (50 g, 0.264 mol). The reaction mixture is stirred at room temperature for 18 hours and then diluted with DCM (1750 ml). The mixture is washed with 10% citric acid (2×500 ml), saturated sodium hydrogen carbonate solution (2×500 ml) and brine (600 ml). The organic portion is dried (MgSO4), concentrated in vacuo and the crude residue is stirred with iso-hexanes (750 ml) for 1 hour. The resulting solid is dissolved in dioxane (400 ml) and treated with 4M HCl in dioxane (350 ml). After 1 hour the precipitate is filtered and washed with dioxane (100 ml) to afford the title compound as the hydrochloride salt [MH+169.84].

1. washThe mixture is washed with 10% citric acid (2×500 ml), saturated sodium hydrogen carbonate solution (2×500 ml) and brine (600 ml)
2. dry with materialThe organic portion is dried (MgSO4)
3. concentrationconcentrated in vacuo
4. stirringthe crude residue is stirred with iso-hexanes (750 ml) for 1 hour
5. dissolutionThe resulting solid is dissolved in dioxane (400 ml)
6. additiontreated with 4M HCl in dioxane (350 ml)
7. filtrationAfter 1 hour the precipitate is filtered
8. washwashed with dioxane (100 ml)

ORD record

ord-56185b12a24640b29d4b5c54ccc1347c

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08053574B2