Sodium Hydroxide → Ammonium Acetate

Participants

Reaction Steps

To a solution of Example 56B (470 mg, ˜0.55 mmol) in 5 mL tetrahydrofuran and 3.5 mL methanol was added aqueous sodium hydroxide (1 M, 2.08 mL, 2.08 mmol). The reaction mixture was stirred at room temperature for 16 hours and concentrated. To the residue was added 2 mL dichloromethane and 1 mL trifluoroacetic acid. The mixture was stirred at room temperature for 40 minutes. The reaction was concentrated then purified by reverse-phase HPLC performed on a Phenomenex Luna C8 AXIA column (30×75 mm, 100 Å) using a gradient of 10% to 95% acetonitrile:10 mM ammonium acetate in water to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.24-2.36 (m, 2 H) 2.97 (t, J=5.65 Hz, 2 H) 3.66-3.71 (m, 2 H) 5.70 (s, 2 H) 6.60-6.69 (m, 2 H) 7.03 (s, 1 H) 7.54-7.69 (m, 2 H) 7.83 (d, J=3.36 Hz, 1 H) 7.88 (d, J=8.24 Hz, 1 H) 8.17 (d, J=8.24 Hz, 1 H) 8.28 (d, J=5.19 Hz, 1 H) 8.41-8.56 (m, 2 H) 11.86 (s, 1 H). MS (ESI) m/e 425 (M+H)+.

Provenance & Evidence