Acetic Anhydride → HCID 136383518, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the product of Example 74G (20 mg, 0.032 mmol) in dichloroethane (0.5 mL), acetic anhydride (5 μL, 0.048 mmol) and triethylamine (13 μL, 0.096 mmol) were added. The reaction solution was heated at 75° C. for 96 h. After cooling to room temperature, the solution was concentrated in vacuo. The resulting residue was dissolved in methanol (0.5 mL) and treated with excess of K2CO3 for 30 min. The mixture was filtered and the filtrate was concentrated in vacuo. The resulting residue was taken up in ethyl acetate (1 mL), washed with aqueous 1 N HCl, dried (Na2SO4), and concentrated in vacuo. Column chromatography on silica (1%→2%→3% methanol/dichloromethane) afforded the title compound as a brown solid (5 mg, 24%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.25-0.42 (m, 1H), 0.47 (s, 9H), 0.73-0.96 (m, 1H), 1.68-2.05 (m, 5H), 3.02 (s, 3H), 5.06 (d, J=18.02 Hz, 1H), 5.24-5.42 (m, 1H), 7.27-7.61 (m, 10H), 7.83 (d, J=6.99 Hz, 1H), 10.01 (s, 1H); MS m/z 665.2 (M+H)+.

Provenance & Evidence