Triethylsilane → 2-Methyl-3-(4-{2-[2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-2-phenoxy-propionic acid ethyl ester

Participants

Reaction Steps

Trifluoroacetic acid (60 mL) is added dropwise to a solution of 3-(4-{2-[3-(4-Methoxy-benzyl)-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-2-methyl-2-phenoxy-propionic acid ethyl ester (3.46 g, 5.0 lmmol) and triethylsilane (1.6 mL, 10.0 mmol, d=0.728). The reaction mixture is stirred at ambient temperature for 2 hours, concentrated, and diluted with ethyl acetate. The solution is washed with a saturated solution of aqueous sodium bicarbonate, water, and brine, then dried over Na2SO4, and concentrated in vacuo to provide the title compound. 1H NMR (400 MHz, CDCl3): δ 7.58 (d, 2H, J=8.2 Hz), 7.38 (d, 2H, J=8.2 Hz), 7.23-7.14 (m, 4H), 6.97 (t, 1H, J=7.4 Hz), 6.82 (d, 2H, J=7.4 Hz), 6.78-(d, 2H, J=7.4 Hz), 4.44, 4.38 (ABq, 2H, J=15.6 Hz), 4.20 (q, 2H, J=7.4 Hz), 4.07-3.99 (m, 2H), 3.96-3.89 (m, 1H), 3.47 (t, 1H, J=8.2 Hz), 3.27, 3.09 (ABq, 2H, J=14.1 Hz), 3.04, 3.02 (ABq, 1H, J=6.7 Hz), 2.08-1.99 (m, 1H), 1.98-1.92 (m, 1H), 1.38 (s, 3H), 1.21 (t, 3H, J=6.7 Hz). MS [EI+] 571 (M+H)+, [EI−] 569 (M−H)+. Rf=0.07 in 33% acetone in hexanes.

Provenance & Evidence