Hydrochloric Acid → HCID 71573271, compound

Participants

Reaction Steps

A mixture of 5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate (50 mg, 0.09 mmol) and LiOH H2O (15 mg, 0.36 mmol) in THF—H2O (1 mL/0.2 mL) was stirred at rt for 1 h and diluted with EA (2 mL). The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure to give a residue that was dissolved in HCl-EtOH (4 N, 5 mL) and H2O (0.3 mL). The mixture was stirred at 35° C. for 20 h. To it was added conc HCl (1.7 mL) and the reaction mixture was stirred at 60° C. for 20 h. The mixture was cooled to rt, concentrated under reduced pressure. The residue was purified by preparative TLC to give the desired title compound (10 mg; yield 27%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.81 (d, J=6.8 Hz, 1 H), 7.68 (s, 1 H), 7.63 (d, J=8.0 Hz, 1 H), 7.51 (s, 2 H), 7.43 (d, J=1.2 Hz, 1 H), 5.13 (s, 2 H), 4.12 (m, 1 H), 3.74 (m, 1 H) ppm; MS: m/z=416 (M+1, ESI+).

Provenance & Evidence