Sodium Hydroxide → (+/-)-3-[4-(2'-Butoxy-5'-methyl-biphenyl-4-ylmethoxy)-phenyl]-3-(4-fluorophenyl)-propionic acid

Participants

Reaction Steps

A mixture of 45.3 (56 mg, 0.1 mmol) and 2N NaOH(aq) solution (0.31 mL, 0.62 mmol) in THF (3 mL) was stirred at room temperature overnight. The reactor mixture was concentrated, treated with dilute HCl, and extracted into ethyl acetate. The organic layer washed with water and concentrated to yield product which was purified by flash chromatography to give compound 45 (40 mg). 1H NMR (500 MHz, CDCl3, ppm), δ 0.9 (t, 3H), 1.4 (m, 2H), 1.65 (m, 2H), 2.35 (s, 3H), 3.05 (m, 2H), 3.9 (t, 2H), 4.5 (t, 1H), 5.05 (s, 2H), 6.8-7.5 (m, 15H). MS ESI (neg.) m/e: 511.0 (M−H).

Provenance & Evidence