Triethylsilane → 2-Butoxy-2-methyl-3-{4-[2-(3-methyl-2-oxo-imidazolidin-4-yl)-ethoxy]-phenyl}-propionic acid ethyl ester

Participants

Reaction Steps

Trifluoroacetic acid (110 mL) is added dropwise to a solution of 2-Butoxy-3-(4-{2-[1-(4-methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-methyl-propionic acid ethyl ester (5.31 g, 10.1 mmol) and triethylsilane (3.22 mL, 20.2 mmol, d=0.728). The reaction mixture is stirred at ambient temperature for 4 h, concentrated in vacuo, and diluted with ethyl acetate. The solution is washed, then dried, concentrated, and purified by flash chromatography to provide the title compound (4.1 g, 100%). 1H NMR (400 MHz, CDCl3): δ 7.09 (d, 2H, J=8.4 Hz), 6.74 (d, 2H, J=8.4 Hz), 5.36 (s, 1H), 4.17-4.07 (m, 2H), 4.02-3.96 (m, 2H), 3.76-3.68 (m, 2H), 3.55 (t, 1H, J=8.8 hz), 3.40-3.31 (m, 2H), 3.20 (t, 1H, J=8.0 Hz), 2.95, 2.91 (ABq, 2H, J=13.6 Hz), 2.76 (s, 3H), 2.24-2.18 (m, 1H), 1.97-1.88 (m, 1H), 1.58-1.51 (m, 2H), 1.41-1.31 (m, 2H), 1.27 (s, 3H), 1.22 (t, 3H, J=7.2 Hz), 0.89 (t, 3H, J=7.2 Hz). Rf=0.44 in 10% CH3OH in CH2Cl2.

Provenance & Evidence