Hydrochloric Acid → 2-(6-(5-Amino-1,3,4-thiadiazol-2-yloxy)-4-chloro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2-(6-(5-amino-1,3,4-thiadiazol-2-yloxy)-4-chloro-1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)acetate (330 mg, 0.89 mmol) in THF (10 mL) and H2O (3 mL) was added LiOH (100 mg, 4.16 mmol). The reaction mixture was stirred at 0° C. for 3 h and acidified with 1N HCl to pH=2-4. The resulting mixture was extracted with EtOAc (2×10 ml). 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 (15 mg, yield 5%). 1H NMR (400 MHz, DMSO-d6) δ 12.45 (s, 1H), 9.57 (s, 1H), 7.56 (m, 2H), 7.20 (s, 2H), 5.51 (m, 1H), 3.22 (m, 1H), 2.32 (s, 3H), 2.36 (m, 1H). MS (ESI) m/z=342 [M+H]+.

Provenance & Evidence