Sodium Bicarbonate → HCID 178428293, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the product of Example 29A (120 mg, 0.17 mmol) in concentrated sulfuric acid (5 mL) was added water (1 mL) at 0° C. and the mixture was heated at 95° C. for 20 minutes. After cooling to ambient temperature, the mixture was diluted with water (3 mL), and the pH was adjusted to pH 8-9 with saturated sodium bicarbonate solution. The mixture was extracted with dichloromethane (3×20 mL). The combined organic phase was concentrated and the residue was purified via preparative HPLC using a gradient of 10/90 to 80/20 acetonitrile/water (containing 0.1% trifluoroacetic acid) to give the title compound. 1H NMR (DMSO-d6, 3 00 MHz): δ 13.55 (br, 1H), 11.66 (s, 1 H), 9.58 (s, 1 H), 8.67 (s, 1 H), 8.57 (s, 1 H), 7.81 (s, 1 H), 7.57-7.54 (m, 1 H), 7.41-7.36 (m, 1 H), 7.11 (dd, J=8.4, 2.1 Hz, 1 H), 7.05 (d, J=2.1 Hz, 1 H), 6.62 (d, J=8.4 Hz, 1 H), 4.69 (s, 2H), 3.23-3.22 (m, 4 H), 2.94-2.92 (m, 4 H), 2.14 (s, 3 H). MS: 510 (M+H+).

Provenance & Evidence