Ethyl Acetate → 3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-5-[(3-methyl-4-oxo-3,4-dihydro-2H-1,3-benzoxazin-7-yl)oxy]benzoic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-hydroxy-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}benzoic acid (175 mg, 0.77 mmol), 7-fluoro-3-methyl-2,3-dihydro-4H-1,3-benzoxazin-4-one (141 mg, 0.77 mmol) and potassium carbonate (321 mg, 2.32 mmol) in acetonitrile (5 mL) was stirred in a microwave reactor at 160° C. for 16 hours then reduced in vacuo and ethyl acetate (50 mL) added. The mixture was washed with water (50 mL), the aqueous layer acidified with 1M citric acid and extracted into ethyl acetate (2×50 mL). The combined organics were washed with brine (50 mL), dried (MgSO4), and reduced in vacuo to give the desired compound as a brown oil (0.24 g). m/z 453 (M+H)+

Provenance & Evidence