Lithium Hydroxide → HCID 178425093, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of EXAMPLE 379B (0.162 g) in tetrahydrofuran (2 mL) and methanol (0.5 mL) was added 1.0 M aqueous LiOH (0.596 mL) and the reaction heated to 50° C. for 1 hour. The reaction was cooled, diluted with dichloromethane (30 mL) and water (5 mL), and quenched with aqueous HCl (1.0 M, 0.6 mL). The aqueous layer was diluted with saturated NH4Cl solution (5 mL) and removed. The organic layer was dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography (Reveleris 40 g) eluting with a gradient of 0.5% to 5% methanol/dichloromethane over 30 minutes (flow=40 mL/minute) provided the title compound. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ 12.00 (s, 1H), 11.68 (s, 1H), 11.38 (s, 1H), 8.55 (d, 2H), 8.04 (d, 1H), 7.79 (dd, 1H), 7.59-7.43 (m, 3H), 7.34 (d, 2H), 7.05 (t, 3H), 6.68 (dd, 1H), 6.39 (dd, 1H), 6.19 (d, 1H), 3.25 (s, 2H), 3.07 (s, 4H), 2.75 (s, 2H), 2.17 (d, 7H), 1.95 (s, 6H), 1.62 (s, 1H), 1.38 (s, 4H), 1.03 (dd, 2H), 0.92 (s, 6H).

Provenance & Evidence