Trichloroacetyl isocyanate → HCID 23648667, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 17F (377 mg, 1.12 mmol) in dichloromethane (10 mL) at 0° C. was added trichloroacetyl isocyanate (145 μL, 1.22 mmol). The mixture was stirred at 0° C. for 10 minutes. The reaction was concentrated and the residue was dissolved in methanol (˜60 mL) and a small amount of Na2CO3 was added. The mixture was stirred at room temperature for 3 hours before being concentrated. The residue was dissolved in dichloromethane, which was washed with water (1×) and concentrated. The residue was purified on silica gel eluting with hexane and ethyl acetate gradient to give the desired product as a white solid (286 mg, 67%), MS (DCI): m/z 382 (M+H); 1H NMR (300 MHz, DMSO-d6) δ ppm 7.78-7.86 (m, 2H), 6.99-7.08 (m, 4H), 6.94-6.99 (m, 2H), 6.75 (s, 1H), 6.61 (d, J=8.46 Hz, 1H), 5.59 (br s, 2H), 4.90-5.02 (m, 1H), 4.53-4.63 (m, 1H), 1.41 (d, J=6.99 Hz, 3H), 1.27 (d, J=5.88 Hz, 6H).

Provenance & Evidence