Triethylamine → 2-bromo-N-(isoxazol-3-yl)acetamide

To a stirred solution of bromoacetylbromide (5.36 ml, 61.6 mmol) in diethylether (100 ml) at −40° C. is added, dropwise over 20 minutes, a solution of 3-aminoisoxazol (5.0 ml, 67.0 mmol) and triethylamine (8.5 ml, 61.4 mmol) in diethylether (20 ml). Additional diethylether (50 ml) is added and stirring continued for 3 hours. The reaction mixture is filtered and the solution then washed with 1 M sodium carbonate solution, 1 M hydrochloric acid and brine. Concentration followed by purification by flash silica column chromatography (ethyl acetate/iso-hexane 4:7) gives the title compound as a white solid.

1. filtrationThe reaction mixture is filtered
2. washthe solution then washed with 1 M sodium carbonate solution, 1 M hydrochloric acid and brine
3. concentrationConcentration
4. customfollowed by purification by flash silica column chromatography (ethyl acetate/iso-hexane 4:7)

ORD record

ord-7b502134a0214c33b339d88195c530e5

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07723356B2