Potassium Carbonate → 2-(4-Cyclohexyl-phenoxy)-2-methyl-3-(4-{2-[5-methyl-2-(3-thiophen-2-yl-phenyl)-oxazol-4-yl]-ethoxy}-phenyl)-propionic acid

Participants

Reaction Steps

A mixture of 2-(4-cyclohexylphenoxy)-3-(4-hydroxyphenyl)-2-methyl-propionic acid ethyl ester (0.030 mmol), toluene-4-sulfonic acid 2-[5-methyl-2-(3-thiophen-2-ylphenyl)oxazol-4-yl]ethyl ester (0.030 mmol) (see Ex. 5, Part B) and 325 mesh K2CO3 (0.084 g, 0.60 mmol) in ethanol (2 mL) was heated to reflux for 24 h under N2. Aqueous 5N NaOH (0.5 mL) and additional ethanol (1 mL) was added to the reaction mixture and it was heated at reflux for an additional 2 h. The reaction was cooled and the solvent removed in vacuo. The residue was acidified with aqueous 1 N HCl (5 mL), extracted with water and CH2Cl2 and the organic layer dried by passing it through a Varian Chem Elut 1003 cartridge. The solvent was removed in vacuo to give 2-(4-cyclohexyl-phenoxy)-2-methyl-3-(4-{2-[5-methyl-2-(3-thiophen-2-yl-phenyl)-oxazol-4-yl]-ethoxy}-phenyl)-propionic acid. 1H NMR (400 MHz, CDCl3) δ 8.21 (s, 1H), 7.88 (d, 1H, J=7.82 Hz), 7.64 (d, 1H, J=7.82 Hz), 7.43 (d, 1H, J=7.82 Hz), 7.41 (dd, 1H, J=3.52 Hz, 1.17 Hz), 7.31 (dd, 1H, J=3.91 Hz, 1.17 Hz), 7.19 (d, 2H, J=8.60 Hz), 7.10–7.06 (m, 3H), 6.84 (d, 2H, J=7.04 Hz), 6.82 (d, 2H, J=8.21 Hz), 4.23 (t, 2H, J=6.65 Hz), 3.22 (d, 1H, J=14.08 Hz), 3.13 (d, 1H, J=14.08 Hz), 2.99 (t, 2H, J=6.65 Hz), 2.39 (s, 3H), 1.81 (d, 5H, J=8.60 Hz), 1.40 (s, 3H), 1.38–1.32 (m, 5H). MS (ES+) m/z mass calcd C38H40NO5S 622.26, found 622.3.

Provenance & Evidence