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

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Reaction Steps

A solution of 3-(4-{2-[1-(4-hydroxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-isopropoxy-propionic acid ethyl ester (0.048 g, 0.089 mmol) in ethanol (8 mL) was treated with aqueous 5 N NaOH (1.5 mL) and stirred at room temperature for 2 h. The solvent removed in vacuo. The resultant residue was acidified with aqueous 1 N HCl (15 mL) and extracted with CH2Cl2. The organic layer was dried (Na2SO4) and the solvent removed in vacuo to afford 0.038 g (84%) 3-(4-{2-[1-(4-hydroxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-isopropoxy- propionic acid. 1H NMR (500 MHz, CDCl3) δ 7.49 (d, 2H, J=8.07 Hz), 7.30 (d, 2H, J=8.07 Hz), 7.06 (d, 2H, J=8.31 Hz), 6.66 (d, 2H, J=8.31 Hz), 4.40, 4.31 (ABq, 2H, J=15.65 Hz), 4.03-4.01 (m, 1H), 3.90 (t, 2H, J=5.87 Hz), 3.59-3.53 (m, 1H), 3.48 (hp, 1H, J=5.87 Hz), 3.31 (t, 1H, J=8.80 Hz), 3.12-2.96 (m, 1H), 2.95 (t, 1H, J=8.80 Hz), 2.90-2.79 (m, 1H), 2.78 (s, 3H), 2.27-2.23 (m, 1H), 1.93-1.84 (m, 1H), 1.14 (d, 3H, J=5.87 Hz), 0.97 (d, 3H, J=5.87 Hz). HRMS (ES+) m/z exact mass calc'd for C26H32N2O5F3 (M+1) 509.2274. Found m/z 509.2263.

Provenance & Evidence