Ethyl Acetate → Ethyl 4-(((2,4-dimethoxybenzyl)(2-ethoxy-2-oxoethyl)amino)methyl)-3-(4-fluorophenyl)isoxazole-5-carboxylate

Participants

Reaction Steps

Ethyl 4-(bromomethyl)-3-(4-fluorophenyl)isoxazole-5-carboxylate (12.4 g, 37.8 mmol) was dissolved in 80 mL of DMF. N-(2,4-dimethoxybenzyl)glycine ethyl ester (9.56 g, 37.8 mmol) and potassium carbonate (5.75 g, 41.6 mmol) were added, and the mixture was stirred at room temperature for 16 h. EtOAc (200 mL) and brine (200 mL) were added and the aqueous layer was extracted with additional EtOAc. The combined organic layer was washed with water and brine, and dried over MgSO4. After solvent was removed in vacuo, the crude product was purified by flash chromatography (0-40% EtOAc/hexanes) to give 8.7 g of the title compound. 1H NMR (CDCl3, 200 MHz): δ=8.00-8.13 (m, 2H), 7.01-7.18 (m, 3H), 6.38-6.45 (m, 2H), 4.48 (q, 2H, J=7.4 Hz), 4.00-4.20 (m, 4H), 3.82 (s, 5H), 3.65 (s, 3H), 3.30 (s, 2H), 1.47 (t, 3H, J=7.0 Hz), 1.20-1.30 (m, 3H).

Provenance & Evidence