Acetic Acid → HCID 67170951, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-hydroxy-2-(3-(4-propylphenyl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)acetonitrile (Preparation 127A, 120 mg, 0.35 mmol) in glacial AcOH (1.5 mL) was added concentrated HCl (0.5 mL). The reaction mixture was stirred at 70° C. for 8 h. After cooling, the solution was poured into water and was extracted with ethyl acetate. The organic layer was dried (over magnesium sulfate), filtered, and concentrated. The resulting residue was purified by preparative HPLC (Phenomenex Luna 5 u C18 21.2×100 mm, Solvent A: 90% water with 10% MeOH and 0.1% TFA, Solvent B: 90% MeOH with 10% water and 0.1% TFA, Gradient: 0% B to 100% B over 10 min, 20 mL/min, 220 nM, product retention time=12.1 min) to give 2-hydroxy-2-(3-(4-propylphenyl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)acetic acid (20 mg, 0.049 mmol, 13% yield): product HPLC ret. time=9.59 min. (condition G); LC/MS M+1=364.1; 1H NMR (400 MHz, CD3OD) δ ppm 7.87 (1H, d, J=7.92 Hz), 7.70 (2H, d, J=8.14 Hz), 7.41-7.57 (2H, m), 7.35 (2H, d, J=8.14 Hz), 5.19 (1H, s), 3.04 (4H, s), 2.66 (2H, t, J=7.59 Hz), 1.60-1.77 (2H, m), 0.97 (3H, t, J=7.26 Hz).

Provenance & Evidence