Potassium Carbonate → HCID 10188807, compound

Participants

Reaction Steps

A mixture of 2-(3-tert-butyl-phenoxy)-3-(4-hydroxyphenyl)-2-methylpropionic acid ethyl ester (0.030 mmol) (see Ex. 23, Part B), toluenesulfonic acid 2-(5-methyl-2-(4-thiophen-2-yl-phenyl)-oxazol-4-yl)ethyl ester (0.030 mmol) (see Ex. 3, 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-(3-tert-butyl-phenoxy)-2-methyl-3-(4-{2-[5-methyl-2-(4-thiophen-2-yl-phenyl)-oxazol-4-yl]-ethoxy)-phenyl)-propionic acid. 1H NMR (400 MHz, CDCl3) δ 7.97 (d, 2H, J=8.60 Hz), 7.67 (d, 2H, J=8.60 Hz), 7.36 (dd, 1H, J=3.91 Hz, 1.17 Hz), 7.33 (dd, 1H, J=3.91 Hz, 1.17 Hz), 7.20–7.16 (m, 3H), 7.12–7.07 (m, 2H), 6.89 (t, 1H, J=1.96 Hz), 6.84 (d, 2H, J=8.60 Hz), 6.72 (dd, 1H, J=8.60 Hz, 2.74 Hz), 4.22 (t, 2H, J=6.65 Hz), 3.25 (d, 1H, J=14.08 Hz), 3.15 (d, 1H, J=14.08 Hz), 3.01 (t, 2H, J=6.65 Hz), 2.40 (s, 3H), 1.43 (s, 3H), 1.26 (s, 9H). HRMS (ES+) m/z exact mass calcd for C36H38NO5S 596.2471, found 596.2454.

Provenance & Evidence