Ethyl Acetate → 3-{4-[3-(Biphenyl-4-yloxy)-propoxy]-2-cyclohexylcarbamoyloxymethyl-phenyl}-propionic acid tert-butyl ester

Participants

Reaction Steps

A mixture of 3-(2-cyclohexylcarbamoyloxymethyl-4-hydroxy-phenyl)-propionic acid tert-butyl ester (50 mg, 0.13 mmol; Example 652 Step D), 4-(3-bromo-propoxy)-biphenyl (58 mg, 0.2 mmol; Tetrahedron 1994, 50, 3427, and potassium carbonate (53 mg, 0.39 mmol) in acetonitrile (6 mL) was heated at 80° C. overnight. Ethyl acetate (20 mL) and H2O (20 mL) were added. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. The crude mixture was purified by silica gel column chromatography (hexane/ethyl acetate 4/1) to give the title compound (50 mg, 65%). 1H-NMR (300 MHz, CDCl3): δ 7.54 (m, 4H), 7.42 (t, 2H, J=7.6), 7.32 (d, 1H, J=8.4), 7.12 (d, 1H, J=8.3), 6.99 (d, 2H, J=8.7), 6.93 (d, 1H, J=2.2), 6.82 (dd, 1H, J=8.4, 2.7), 5.09 (s, 2H), 4.74 (d, 1H, J=7.5), 4.18 (m, 4H), 3.56-3.42 (m, 1H), 2.90 (t, 2H, J=7.8), 2.48 (t, 2H, J=7.8), 2.28 (qn, 2H, J=6.0), 1.95-1.88 (m, 2H), 1.75-1.08 (m, 8H), 1.44 (s, 9H).

Provenance & Evidence