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

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Reaction Steps

To a solution of ethyl 2-(6-(4-cyanopyridin-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 of water). After stirring at room temperature for two hours, the reaction mixture was evaporated and then acidified to pH 5 using 1 N HCl and then concentrated. HPLC purification gave desired product as a white powder. 1H NMR (400 MHz, DMSO-d6) δ 12.2 (b, 1H), 9.24 (b, 1H), 8.30 (d, J=5.2 Hz, 1H), 7.57 (s, 1H), 7.50 (dd, J=5.2, 1.2 Hz, 1H), 7.17 (d, J=2 Hz, 1H), 7.01 (d, J=1.6 Hz, 1H), 5.45 (dd, J=9.6, 2 Hz, 1H), 3.02 (dd, J=15.6, 2.4 Hz, 1H), 2.46 (s, 3H), 2.08 (dd, J=16, 10 Hz, 1H). MS (ESI) m/z=323 [M−H]+.

Provenance & Evidence