Sodium Carbonate → HCID 71113010, compound

Participants

Reaction Steps

4-[(3,3-dimethyl-1,3-dihydro-2-benzofuran-5-yl)oxy]aniline (Intermediate 70, 120 mg, 0.47 mmol) and methyl-D-isovalinic acid hydrochloride (80 mg, 0.52 mmol) were suspended in a mixture of acetonitrile (1.5 mL) and ethyl acetate (0.5 mL). A 50% w/w solution of T3P in ethyl acetate (1.1 equiv) was added drop wise. The reaction mixture was stirred for 30 minutes at room temperature and then at 80° C. for 4 hours. The reaction mixture was cooled to room temperature and treated with ethyl acetate and saturated Na2CO3 solution and stirred vigorously for 10 min. Two layers were separated and the organic layer was washed twice with brine, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography on silica gel using dichloromethane/Methanol from 100:0 to 90:10 as eluent to afford the title compound (140 mg).

Provenance & Evidence