Sodium Hydroxide → 3-(4-{2-[1-(3-Methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-methyl-2-phenoxy-propionic acid

Participants

Reaction Steps

A solution of 3-(4-{2-[1-(3-methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-methyl-2-phenoxy-propionic acid ethyl ester (0.28 g, 0.51 mmol) in ethanol (20 mL) is treated with aqueous 5 N NaOH (2 mL) and heated to reflux 1 h. The reaction mixture is cooled, the solvent removed in vacuo. The resultant residue is acidified with aqueous 1 N HCl (20 mL) and extracted with CH2Cl2. The organic layer is dried (Na2SO4) and the solvent removed in vacuo to afford 0.257 g (97%) 3-(4-{2-[1-(3-methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-methyl-2-phenoxy-propionic acid 1H NMR (500 MHz, CDCl3) □ 7.28-7.20 (m, 3H), 7.18 (d, 2H, J=8.80 Hz), 7.04 (t, 1H, J=7.34 Hz), 6.91 (d, 2H, J=7.83 Hz), 6.82 (t, 1H, J 7.83 Hz), 6.79-6.78 (m, 2H), 6.73 (d, 2H, J=8.83 Hz), 4.38, 4.28 (ABq, 2H, J=14.92 Hz), 3.95 (t, 2H, J=5.87 Hz), 3.77 (s, 3H), 3.60 (ddd, 1H, J=12.2 Hz, J=8.40 Hz, J=3.42 Hz), 3.36 (t, 1H, J=7.83 Hz), 3.30, 3.10 (ABq, 2H, J=13.69 Hz), 2.96 (t, 1H, J=7.83 Hz), 2.83 (s, 3H), 2.25-2.18 (m, 1H), 1.92-1.84 (m, 1H), 1.42 (s, 3H). HRMS (ES+) m/z exact mass calc'd for C30H35N2O6 (M+1) 519.2495. Found m/z 519.2504.

Provenance & Evidence