Hydrochloric Acid → HCID 88385605, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of the compound of part (e) (215 mg) and dichloromethane (3 ml) cooled to -78° C. under argon, was added with stirring dry triethylamine (70 μl). To the resulting solution was added succinic anhydride (50 mg) and 4-dimethylaminepyridine (5 mg), and the mixture was allowed to warm to room temperature. The mixture was stirred at room temperature for a further 3 hours before pouring into aqueous 2N hydrochloric acid (4 ml). The organic layer was separated, and the aqueous layer extracted with ethyl acetate. The combined organic layers were dried (MgSO4) and evaporated. The residue was treated with one equivalent of aqueous sodium hydroxide, sufficient acetonitrate added to render the mixture homogeneous, and the resulting solution freeze dried. The resulting solid was dissolved in ethyl acetate (1 ml) and petroleum ether (10 ml) added. The mixture was boiled to half volume, and the solid product collected by filtration, and dried in-vacuo to afford the title compound. 1N NMR (360 MHz; D6 -DMSO) δ2.15 (2H, m), 2.25 (2H, m), 2.72 (1H, m), 2.87 (4H, m), 3.05 (1H, dd, J=5.7, 14.5 Hz), 4.42 (1H, m), 6.97 (1H, t, J=7.8 Hz), 7.05 (1H, t, J=8.0 Hz), 7.18 (1H, d, J=2.2 Hz), 7.32 (1H, d, J=8.3 Hz), 7.48 (1H, d, J=7.7 Hz), 7.79 (2H, s), 7.85 (1H, s), 9.00 (1H, d, J=6.8 Hz), 10.90 (1H, s); m/e (CI+) 528 (MH+). Found: C, 52.12; H, 3.99; N, 4.67. C25H21F6 N2O4Na.1.5(H2O) requires C, 52.00; H, 4.19; N, 4.85%.

Provenance & Evidence