Hydrogen Peroxide → HCID 44545782, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of Example 8) (24 mg, 0.05 mmol) in acetic acid (0.5 mL) at room temperature was added H2O2 (30% aq.) and the solution heated to 100° C. for 23 h. The acetic acid was removed in vacuo and the brown oil partitioned between NaHCO3 (20 mL) and EtOAc (20 mL). The aqueous phase (pH=10) was extracted with EtOAc (2×10 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo. The product was purified by column chromatography (silica gel, hexane/Et2O (1:4) to Et2O to MeOH/DCM (1:19)). The title compound (10 mg, 41%) eluted from the column with MeOH/DCM (1:19) as a pale yellow oil. 1H NMR (CDCl3): δ 8.26-8.24 (m, 1H), 7.41-7.38 (m, 1H), 7.21 (m, 4H), 7.00-6.94 (m, 2H), 4.44 (t, J=6 Hz, 2H), 4.22-4.15 (m, 2H), 3.32 (t, J=6 Hz, 2H), 3.05-2.95 (m, 1H), 2.57 (s, 3H), 3.37 (s, 3H), 2.34 (s, 3H), 2.10-1.90 (m, 2H), 1.30 (d, J=6.9 Hz, 3H), ESIMS m/z [M+H]+ 493.2.

Provenance & Evidence