Trifluoroacetic acid → HCID 86270805, compound

Participants

Reaction Steps

To a solution of Example 34d (0.023 g, 0.038 mmol) in dichloromethane was added TFA (0.5 mL, 6.49 mmol). The reaction mixture was stirred at ambient temperature for 1 hour and then concentrated by rotary evaporation. The residue was concentrated down from toluene (2×), then taken up in methanol/tetrahydrofuran. Sodium acetate (0.124 g, 1.514 mmol) was added, and the reaction mixture was heated at reflux for 2 hours. The reaction mixture was concentrated by rotary evaporation. The residue was partitioned between ethyl acetate and water. The layers were separated, and the organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography (silica gel, 20-80% ethyl acetate in hexanes) to give the title compound (0.004 g, 22% yield). 1H NMR (300 MHz, DMSO-d6) δ 12.20-12.46 (m, 1 H), 9.06 (s, 1 H), 8.41-8.52 (m, 1 H), 7.82 (d, J=2.03 Hz, 1 H), 7.66 (dd, J=8.82, 1.70 Hz, 1 H), 7.44-7.54 (m, 2 H), 7.15-7.23 (m, 2 H), 6.99 (d, J=8.48 Hz, 1 H), 2.74 (d, J=4.41 Hz, 3 H), 2.65 (s, 3H). MS (ESI+) m/z 478.0)+.

Provenance & Evidence