Sodium Bicarbonate → HCID 178462328, compound

Participants

Reaction Conditions

Reaction Steps

The thioether of Example 76 (155 mg, 0.28 mmol) was dissolved in trifluoroacetic acid (800 μl) cooled to 0° C. and treated with a 2.0M solution of trifluoroperacetic acid in trifluoroacetic acid (153 μl, 0.308 mmol), with stirring for 30 minutes. The reaction mixture was poured into 0.5M sodium bicarbonate solution (50 ml), extracted with dichloromethane (3×15 ml), dried (MgSO4) and concentrated in vacuo. The resulting crude solid (200 mg) was purified by flash silica gel chromatography in 8% methanol:dichioromethane to yield the title compound as unresolved stereoisomers as a white foam (81 mg, 51%). 1H NMR (360 MHz, CDCl3) δ 1.44 and 1.46 (3H total, 2×d, J=6.6 Hz), 2.24 (6H, s), 2.56 (1H, m), 2.59 and 2.62 (3H total, 2×s), 2.88 (1H, d, J=11.9 Hz), 3.23 and 3.26 (1H total, 2×d, J=13.9 Hz), 3.42-3.55 (3H, m), 3.62 (1H, br d, J=11.3 Hz), 3.75 and 3.79 (1H total, 2×d, J=14.4 Hz), 4.22 (1H, m), 4.32 and 4.35 (1H total, 2×d, J=2.7 Hz), 4.89 (1H, m), 6.85 (1/2H, s), 7.04-7.13 (3H, m), 7.24 (1/2H, s), 7.50 (2H, br s), 7.73 and 7.75 (1H total, 2×s); MS (ES+) m/z 570 (M+1, 100%).

Provenance & Evidence