Lithium Hydroxide → HCID 178515281, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 119b (150 mg, 0.210 mmol) and lithium hydroxide (50 mg, 2.10 mmol) in i-propanol/THF (1:1, 4 mL) and water (1 mL) was stirred at 30° C. for 1 h. The mixture was evaporated in vacuo and the residue was diluted with water (5 mL). It was then extracted with ethyl acetate (2×10 mL). The combined ethyl acetate extract was concentrated under reduced pressure and the residue was purified by reverse-phase prep-HPLC to afford 119 (85 mg, 58%) as a yellow solid. MS-ESI: [M+H]+ 681.3. 1H NMR (500 MHz, CDCl3) δ 12.72 (s, 1H), 8.45 (s, 1H), 7.93 (d, J=7.5 Hz, 1H), 7.79 (s, 1H), 7.72 (d, J=9.0 Hz, 2H), 7.12 (d, J=8.0 Hz, 1H), 6.98 (d, J=9.0 Hz, 2H), 4.74-4.67 (m, 6H), 4.09-4.04 (m, 1H), 3.78-3.73 (m, 1H), 3.57 (t, J=6.5 Hz, 1H), 3.24-3.22 (m, 4H), 2.99-2.93 (m, 1H), 2.88-2.83 (m, 3H), 2.53-2.51 (m, 6H), 1.93-1.81 (m, 5H).

Provenance & Evidence