Compound G6

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InChIKey JRKYQYSGLMMAFE-UHVFKWDWSA-N

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

An oven-dried vial with stir bar was loaded with G19 (51.4 mg, 0.15 mmol) and dissolved in dichloromethane (4 mL). The reaction was cooled to 0 °C in an ice bath, and sodium carbonate (127.1 mg, 1.20 mmol) and peracetic acid (32% in acetic acid, 170 µL, 0.81 mmol) were added. The reaction stirred for 15 hours, during which time it was allowed to warm to room temperature. Saturated aqueous sodium bicarbonate was added to quench the reaction. The reaction was acidified to pH 3, and the aqueous layer was extracted with ethyl acetate (3x). The combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated. Purification by flash silica chromatography (3:1 to 2:1 hexanes/ethyl acetate) afforded G6 as a white solid (16.0 mg, 30% yield). Unreacted starting material was also recovered as a white solid (7.7 mg). ¹H NMR (CDCl₃, 500 MHz): δ 7.21 (t, J = 7.5 Hz, 1H), 7.07 (d, J = 7.6 Hz, 1H), 7.03 (d, J = 7.4 Hz, 1H), 5.64 (t, J = 6.0 Hz, 1H), 3.47 (s, 1H), 3.24 (dt, J = 13.1, 6.4 Hz, 1H), 3.13 (ddd, J = 13.2, 7.1, 5.8 Hz, 1H), 2.95 (d, J = 17.5 Hz, 1H), 2.90 (d, J = 6.5 Hz, 1H), 2.72 (dd, J = 17.5, 2.8 Hz, 1H), 2.35 - 2.19 (m, 1H), 2.22 (s, 3H), 1.94 (ddt, J = 15.3, 12.1, 5.8 Hz, 1H), 1.89 - 1.77 (m, 2H), 1.68 (dd, J = 14.0, 2.9 Hz, 1H), 1.49 - 1.37 (m, 2H), 1.33 (s, 3H), 0.96 (s, 3H), 0.94 (s, 3H). ¹³C NMR (CDCl₃, 125 MHz): δ 171.5, 169.2, 144.4, 137.9, 136.0, 129.9, 128.1, 119.8, 81.8, 60.2, 48.3, 47.5, 46.9, 40.6, 35.9, 33.1, 29.9, 29.1, 28.6, 20.5, 19.6, 19.0. HRMS(ESI): m/z calc. for C₂₂H₃₀NO₃ [M+H]⁺: 356.2226, found: 356.2219.