Sodium Hydroxide → 2-(6-(6-Chloropyridin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetic acid

Participants

Reaction Steps

To a solution of ethyl 2-(6-(6-chloropyridin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate in MeOH/THF (6 mL, 1:1) was added aqueous NaOH solution (100 mg in 1.5 mL of water). After stirring at room temperature for two hours, the reaction mixture was evaporated and then acidified to pH 3 using 1 M HCl. This was then extracted with EtOAc, the organic layers were combined, washed by brine and concentrated. HPLC purification gave desired product as a white powder. 1H NMR (400 MHz, DMSO-d6) δ 9.2 (b, 1H), 7.90 (t, J=7.6 Hz, 1H), 7.24 (m, 2H), 7.09 (s, 1H), 7.00 (d, J=8.4 Hz, 1H), 5.54 (dd, J=9.6, 2 Hz, 1H), 3.10 (dd, J=15.6, 2.4 Hz, 1H), 2.32 (s, 3H), 2.17 (dd, J=15.6, 9.6 Hz, 1H). 1 proton assumed to be exchanged with solvents. MS (ESI) m/z=332 [M−H]+.

Provenance & Evidence