Trifluoroacetic acid → HCID 10791078, compound

Participants

Reaction Steps

Under argon, 8 (271 mg, 0.422 mmol) was added to a mixture of trifluoroacetic acid (770 mg, 6.7 mmol), CH2Cl2 (3.0 mL), and triethylsilane (330 mg, 2.8 mmol); this was stirred at room temperature for 23 hours. The reaction mixture was concentrated; the resultant oil was dissolved in water (5.0 mL) and adjusted to pH 7 with saturated NaHCO3 solution. This solution was then concentrated; the residue was purified by chromatography on a C-18 column (30% acetone/water, followed by 55% acetone/water) to give 9 (137 mg, 67%) as a colorless oil: 1H NMR (19.7° C.) δ1.30-1.66 (m, 8 H), 1.78 (m, 2 H), 3.09 (m, 2 H), 3.20-3.33 (m, 4 H), 3.45 (m, 1 H), 5.05(s, 2H), 5.09 (s, 2 H), 7.26-7.37 (m, 10 H); HRMS m/z calcd for C26H36N3O6 486.2604, found 486.2614.

Provenance & Evidence