Hydrochloric Acid → HCID 58292851, compound

Participants

Reaction Steps

To a solution of ethyl 2-(4-(cyanomethoxy)-1-hydroxy-6-(pyrazin-2-yloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (100 mg, 0.271 mmol) in EtOH (4 mL) was added an aqueous solution of lithium hydroxide (21.9 mg, 0.54 mmol) in water (1 mL). The reaction mixture was stirred at room temperature overnight and acidified with 1N HCl to pH=3. The resulting mixture was extracted with EtOAc (2×20 mL) and the combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by prep HPLC to give the title compound as a white powder (30 mg. Yield: 26%). 1H NMR (400 MHz, DMSO-d6) δ 12.34 (s, 1H), 9.31 (s, 1H), 8.55 (s, 1H), 8.40 (d, J=2.4 Hz, 1H), 8.23 (t, J=1.2 Hz, 1H), 7.06 (d, J=1.2 Hz, 1H), 7.00 (s, 1H), 5.51 (m, 1H), 4.48 (m, 2H), 4.16 (m, 2H), 3.37 (d, J=2.0 Hz, 1H), 2.21 (m, 1H), 1.16 (m, 3H). MS (ESI) m/z=389 [M+H]+.

Provenance & Evidence