Trifluoroacetic acid → HCID 22458860, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of the product of Example 24 (0.466 g, 0.980 mmol) stirring in dichloromethane (24 mL) at 0° C. was added triethylsilane (0.94 mL, 5.8 mmol). After 10 minutes, trifluoroacetic acid (6.4 mL) was added at such a rate that the temperature was maintained below 5° C. The resulting solution was stirred at 0° C. for 2 hours, then quenched by pouring it into a saturated aqueous sodium bicarbonate solution (50 mL). Methanol was added as necessary to dissolve any residue. This mixture was then extracted with ethyl acetate (2×200 mL). The combined extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated. Purification by radial chromatography (4 mm, silica gel, 8:2 ethyl acetate/methanol) gave 0.304 g (68%) of the title compound as a white foam: 1H NMR (300 MHz, MeOD-d4) δ7.26-7.30 (m, 3H), 7.18 (d, 1H, J=2.2 Hz), 7.03 (d, 2H, J=8.6 Hz), 6.74-6.83 (m, 5H), 4.07-4.11 (m, 4H), 3.00-3.20 (m, 4H), 2.80-2.85 (m, 1H), 2.35-2.41 (m, 2H), 2.05-2.18 (m, 1H), 1.43-1.48 (m, 1H), 1.06 (t, 3H, J=6.2 Hz); IR (KBr) 3385, 2958, 1677, 1610, 1509, 1239, 837 cm−1; MS (FD) m/z 460 (m+).

Provenance & Evidence