Trifluoroacetic acid → HCID 178490674, compound

Participants

Reaction Steps

A solution of Example 15B (295 mg, 0.6 mmol) in CH2Cl2 (5 mL) was treated with trifluoroacetic acid (1 mL) and the reaction mixture was stirred at room temperature for 48 hrs, concentrated on the rotovap and the residue was partitioned between ethyl acetate and saturated NaHCO3. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography using an Analogix® Intelliflash280™ (SiO2, 0-15% methanol in CH2Cl2) to afford the title compound (160 mg, 68% yield). MS (DCI) m/z 394 (M+H)+. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.17-1.27 (m, 2H), 1.28-1.35 (s, 9H), 2.05-2.19 (m, 1H), 2.19-2.34 (m, 1H), 3.45-3.61 (m, 1H), 3.72-3.82 (m, 3H), 4.20-4.35 (m, 3H), 7.11 (d, J=8.7 Hz, 1H), 7.30 (s, 1H), 7.45 (dd, J=8.7, 2.8 Hz, 1H), 7.61 (d, J=2.8 Hz, 1H). MS (DCI) m/z 394 (M+H)+.

Provenance & Evidence