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

Participants

Reaction Steps

A mixture of 2-(4-fluorophenoxy)-3-(4-hydroxyphenyl)-2-methyl-propionic acid ethyl ester (0.030 mmol), toluene-4-sulfonic acid 2-(2-biphenyl-3-yl-5-methyloxazol-4-yl)ethyl ester (0.030 mmol) (see Ex. 2, Part F) 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 3-{4-[2-(2-biphenyl-3-yl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl}-2-(4-fluoro-phenoxy)-2-methyl-propionic acid 1H NMR (400 MHz, CDCl3) δ 8.21–8.20 (m, 1H), 7.94–7.92 (m, 1H), 7.65–7.62 (m, 2H), 7.50–7.34 (m, 4H), 7.17 (d, 2H, J=8.60 Hz), 6.93–6.77 (m, 7H), 4.21 (t, 2H, J=6.65 Hz), 3.20 (d, 1H, J=14.00 Hz), 3.13 (d, 1H, J=14.00 Hz), 3.01 (t, 2H, J=6.65 Hz) 2.40 (s, 3H), 1.37 (s, 3H); HRMS (ES+) m/z exact mass calcd for C34H31NO5F 552.2186, found 552.2175.

Provenance & Evidence