Hydrochloric Acid → HCID 58292721, compound

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Reaction Steps

A solution of [6-(2-dimethylamino-pyrimidin-4-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.094 g, 0.25 mmol) in THF (5 mL) was treated with lithium hydroxide (0.029 g, 1.27 mmol) in water (0.5 mL) at 0° C. The solution was stirred at 0° C. to room temperature for 2 hours, then acidified with 2N HCl to pH 2, and concentrated. The residue was purified by silica gel flash column chromatography (AcOH:acetone:hexanes; trace:1:2; then MeOH:CH2Cl2; 5:95) to give [6-(2-dimethylamino-pyrimidin-4-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid as a white solid after lyophilization (0.02 g, 23%). 1H NMR (400 MHz, DMSO-d6) δ 8.18 (d, J=5.47 Hz, 1H), 7.24 (s, 1H), 7.07 (s, 1H), 6.01 (d, J=5.47 Hz, 1H), 5.50-5.45 (m, 1H), 3.02 (dd, J=15.63, 2.40 Hz, 1H), 2.96 (s, 6H), 2.28 (s, 3H), 2.11 (dd, J=15.63, 9.38 Hz, 1H). MS (ESI) m/z: 344 [M+1].

Provenance & Evidence