Hydrochloric Acid → HCID 86653983, compound

Participants

Reaction Conditions

Reaction Steps

To a solution [6-(6-cyano-pyrimidin-4-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (0.2 g, 0.556 mmol) in THF (3 mL) was added a solution of LiOH (0.041 g, 1.69 mmol) in water (3 mL) at 0° C. The resulting mixture was stirred at 0° C. for 5 hours, acidified to pH 2 using 6M hydrochloric acid and extracted with EtOAc. The organic extracts were washed with water, brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by preparative HPLC to give [6-(6-cyano-pyrimidin-4-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid as a white solid (0.015 g). 1H NMR (400 MHz, DMSO-d δ 9.18 (s, 1H), 8.82 (d, J=10.0 Hz, 1H), 7.45 (d, J=6.0 Hz, 1H), 7.30 (s, 1H), 7.16 (s, 1H), 5.51 (m, 1H), 3.07 (m, 1H), 2.31 (s, 3H), 2.16 (m, 1H). MS (ESI) m/z: 324 [M−1]−. HPLC purity: 96.94% (Maxplot), 98.24% (220 nm).

Provenance & Evidence