Sodium Hydroxide → HCID 58292806, compound

Participants

Reaction Steps

To a solution of ethyl 2-(6-(2-chloropyridin-4-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), 8.23 (d, J=6 Hz, 1H), 7.22 (s, 1H), 7.09 (s, 1H), 6.95 (s, 1H), 6.88 (dd, J=6, 2 Hz, 1H), 5.49 (dd, J=9.2, 2.4 Hz, 1H), 3.04 (dd, J=15.6, 2.8 Hz, 1H), 2.28 (s, 3H), 2.13 (dd, J=15.2, 9.2 Hz, 1H). 1 proton assumed to be exchanged with solvents. MS (ESI) m/z=332 [M−H]+.

Provenance & Evidence