Sodium Hydroxide → HCID 58292847, compound

Participants

Reaction Steps

To a solution of ethyl 2-(6-(5-(aminomethyl)pyridin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (1.18 g, 3.31 mmol) in MeOH/THF (12 mL, 1:1) was added aqueous NaOH solution (250 mg in 3 mL water). After stirring at room temperature for two hours, the reaction mixture was evaporated and then acidified to pH 3 using 1 M HCl. The precipitate was collected and washed with water and dried to give the product as a white solid (0.85 g, yield 78%). No right mass was observed and the structure was confirmed by NMR. 1H NMR (400 MHz, DMSO-d6) δ 12.4 (b, 1H), 9.80 (b, 2H), 9.22 (s, 1H), 8.26 (d, J=2 Hz, 1H), 8.07 (m, 1H), 7.21 (d, J=2 Hz, 1H), 7.08 (d, J=8.4 Hz, 1H), 7.01 (m, 1H), 5.51 (dd, J=9.2, 4 Hz, 1H), 4.15 (s, 2H), 3.07 (dd, J=15.6, 2.4 Hz, 1H), 2.28 (s, 3H), 2.12 (dd, J=15.2, 9.6 Hz, 1H).

Provenance & Evidence