Lithium Hydroxide → 2-(6-(5-Carbamoyl-1,3,4-thiadiazol-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 ethyl 2-(6-(5-carbamoyl-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (0.448 mmol) in THF (3 mL) was added a solution of LiOH (2.24 mmol) in water (3 mL) at 0° C. The resulting mixture was stirred at room temperature for 3 hours then concentrated in vacuo. The residue was purified by preparative HPLC then lyophilized to give 2-(6-(5-carbamoyl-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetic acid as an off white solid (17%). 1H NMR (400 MHz, DMSO-d6) δ 12.32 (s, 1H), 9.31 (s, 1H), 8.44 (s, 1H), 8.07 (s, 1H), 7.48 (s, 1H), 7.36 (s, 1H), 5.54 (dd, 1H), 3.07 (dd, 1H), 2.32 (s, 3H), 2.18 (dd, 1H). MS (ESI) m/z: 348.1 [M−1]−.

Provenance & Evidence