Water → HCID 178491569, compound

Participants

Reaction Conditions

Reaction Steps

The product of Example 30E (80 mg, 0.12 mmol) was dissolved in concentrated sulfuric acid (3 mL) and water (0.5 mL) was added and the solution was heated at 85° C. for 0.5 hours. After cooling to ambient temperature, the mixture was neutralized with saturated aqueous sodium bicarbonate solution and extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated and purified by preparative HPLC using a gradient of 10/90 to 75/25 acetonitrile/water (containing 0.1% trifluoroacetic acid) to give the title compound. 1H NMR (DMSO-d6, 300 MHz): δ 14.11 (s, 1 H), 11.83 (s, 1 H), 9.59 (s, 1 H), 8.59 (s, 1 H), 7.71-7.68 (m, 2 H), 7.60-7.58 (m, 2 H), 7.44 (t, J=7.8 Hz, 1 H), 6.77 (s, 1 H), 6.31 (d, J=8.1 Hz, 1 H), 4.79 (s, 2 H), 3.81 (s, 3 H), 3.51 (s, 2 H), 3.46 (t, J=6.6 Hz, 2 H), 3.33 (t, J=6.3 Hz, 2 H), 1.93-1.78 (m, 4 H). MS: 553 (M+H+).

Provenance & Evidence