Trifluoroacetic acid → 5-(6-(5-(4-Fluorobenzyl)isoxazol-3-yl)-2-(4-fluorophenyl)-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoic acid

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Reaction Steps

TFA (2 mL, 26.0 mmol) was added to a stirred, room temperature mixture of tert-butyl 5-(6-(5-(4-fluorobenzyl)isoxazol-3-yl)-2-(4-fluorophenyl)-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate (100 mg, 0.175 mmol) in dichloromethane (2 mL) and the mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated to dryness and the residue was purified by column chromatography on silica gel, eluting with CH2Cl2/MeOH=10:1 to give 5-(6-(5-(4-fluorobenzyl)isoxazol-3-yl)-2-(4-fluorophenyl)-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoic acid (75 mg, 0.146 mmol) as a yellow solid. LCMS [M+H]+=515. 1H NMR (500 MHz, CDCl3) δ ppm: 8.42 (d, J=8.51 Hz, 1H), 7.93 (d, J=1.26 Hz, 1H), 7.81 (d, J=1.58 Hz, 1H), 7.17-7.37 (m, 6H), 7.09 (t, J=8.51 Hz, 2H), 6.49 (s, 1H), 6.33 (s, 1H), 4.17 (s, 2H), 2.22-2.39 (m, 4H), 1.38-1.65 (m, 4H).

Provenance & Evidence