Lithium hydroxide, monohydrate → HCID 71711649, compound

Participants

Reaction Steps

Lithium hydroxide monohydrate (0.0045 g, 0.107 mmol) was added to a mixture of [6-fluoro-4-(5-methanesulfonyl-pyridin-2-yl)-3-methyl-naphthalen-2-yl]acetic acid methyl ester (0.014 g, 0.036 mmol) in a 1:1 mixture of THF—H2O mixture (2 mL). The reaction mixture was stirred for 5 hours at room temperature. The reaction mixture was concentrated to remove the THF, and the aqueous residue was combined with a 1.0 N aqueous solution of hydrochloric acid. The resulting mixture was extracted with ethyl acetate. The collected organic layers were dried over anhydrous MgSO4, filtered, and concentrated to provide [6-fluoro-4-(5-methanesulfonyl-pyridin-2-yl)-3-methyl-naphthalen-2-yl]acetic acid (0.009 g) as a white solid. The final product contained a significant amount of water as an impurity. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.35 (br. s, 1 H), 9.26 (dd, J=2.42, 0.60 Hz, 1 H), 8.49 (dd, J=8.00, 2.26 Hz, 1 H), 8.03 (dd, J=8.80, 6.80 Hz, 1 H), 7.95 (s, 1 H), 7.73 (d, J=8.15 Hz, 1 H), 7.40 (td, J=8.80, 2.40 Hz, 1 H), 6.75 (dd, J=11.00, 2.40 Hz, 1 H), 3.87 (s, 2 H), 3.45 (s, 3 H), 2.07 (s, 3 H). MS calcd. for C19H17FNO4S [(M+H)+] 374, obsd. 374.0.

Provenance & Evidence