Lithium Hydroxide → 2-{3-[3-(2-Ethyl-5-hydroxy-4-oxazol-4-yl-phenoxy)propoxy]-2-propyl-phenoxy}benzoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-{3-[3-(2-ethyl-5-hydroxy-4-oxazol-4-yl-phenoxy)propoxy]-2-propylphenoxy}benzoic acid methyl ester (89 mg, 0.14 mmol) in methanol (2 mL) was added 1 M lithium hydroxide solution (0.28 mL) and the resulting mixture warmed at 60° C. for 3.5 h. The mixture was cooled to room temperature and concentrated in vacuo. The aqueous residue was diluted with water and the pH adjusted to ˜4. The mixture was extracted three times with methylene chloride. The combined organic extracts were dried (sodium sulfate), filtered, and concentrated in vacuo to provide 27 mg (92%) of the title compound as a yellow solid. 1H NMR (DMSO-d6) δ 12.83 (bs, 1H), 10.12 (bs, 1H), 8.39 (s, 1H), 8.25 (s, 1H), 7.78 (dd, J=8, 1 Hz, 1H), 7.64 (s, 1H), 7.47 (t, J=8 Hz, 1H), 7.16 (m, 2H), 6.80 (t, J=8 Hz, 2H), 6.56 (s, 1H), 6.35 (d, J=8 Hz, 1H), 4.20 (t, J=6 Hz, 2H), 4.12 (t, J=6 Hz, 2H); 2.54 (m, 4H), 2.24 (quintet, J=6 Hz, 2H), 1.43 (hextet, J=8 Hz, 2H), 1.10 (t, J=8 Hz, 3H), 5 0.80 (t, J=8 Hz, 3H); TOF MS ES+ exact mass calculated for C30H32NO7 (p+1): m/z=518.2179. Found: 518.2206; IR (KBr, cm−1) 2961, 1696, 1460, 1222. Anal. Calcd for C30H31NO7: C, 69.62; H, 6.04; N, 2.71. Found: C, 68.71; H. 5.82; N, 2.65.

Provenance & Evidence