Potassium Carbonate → HCID 178490683, compound

Participants

Reaction Steps

To a solution of Example 60A (110 mg, 0.298 mmol) in CH2Cl2 (2 mL) was added trichloroacetyl isocyanate (67.4 mg, 0.358 mmol) and the mixture was stirred for 2 hr. The reaction was concentrated and dissolved in methanol (0.5 mL). A solution of potassium carbonate (140 mg, 1.013 mmol) in water was added and the mixture was stirred for 24 hr. The reaction was concentrated, partitioned between ethyl acetate (3×10 mL) and water (10 mL). The organics were combined, dried, filtered, concentrated and the residue was trituated with CH2Cl2 and hexane (1:3). The solid was collected by filtration (80 mg, 70%). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.32 (s, 9H) 3.79 (s, 3H) 4.29-4.38 (m, 4H) 6.55 (s, 1H) 7.10 (d, J=9.12 Hz, 1H) 7.19 (s, 1H) 7.44 (dd, J=9.12, 2.78 Hz, 1H) 7.67 (d, J=2.78 Hz, 1H); MS (DCI) m/z 412 (M+H)+. Anal calcd C18H22ClN3O4S.0.5 H2O: C, 51.36; H, 5.51; N, 9.98. Found: C, 51.23; H, 5.33; N, 9.92.

Provenance & Evidence