Phosphoric Acid → 2-(2-Benzoylphenylamino)-3-(4-benzyloxyphenyl) propanoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 185 mg (0.62 mmol) of Intermediate 2 in 8 mL (1:1; dioxane:water) was added 500 mg (11.9 mmol) lithium hydroxide monohydrate. The resulting suspension was stirred at 50° C. for 5 h and then cooled to RT. A 1M phosphoric acid solution was added until pH was 5.5 was reached where upon the resulting suspension was extracted with EtOAc (2×25 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated and chromatographed on silica gel using CH2Cl2/MeOH (9:1) to yield 133 mg of the title compound. 1H NMR (CDCl3) δ 8.87 (bs, 1H) 7.60-7.58 (d, 2H, J=6) 7.94-7.32 m (10H), 7.23-7.21 (d, 2H, J=3.9), 6.90-6.88 (m, 2H) 6.67-6.56 (m, 2H), 4.98 (s, 2H), 4.39 (m, 1H), 3.30-3.10 (m, 2H); low resolution MS (FAB+) m/e (MH+) 452.1.

Provenance & Evidence