Compound A8

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InChIKey ONELUWCRBYGKFA-GLOZSXEUSA-N

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

Adrenosterone (2.29 g, 7.61 mmol) was dissolved in isopropanol (30 mL) and sodium carbonate (914 mg, 8.62 mmol) was added to the resulting solution. The reaction mixture was heated to reflux. A solution of sodium periodate (9.14 g, 42.7 mmol) and catalytic potassium permanganate (69 mg, 0.44 mmol) in water (25 mL) was preheated at 75 °C and added to the reaction mixture dropwise using a slow addition funnel over a 30 minute period. The slow addition funnel was then removed and a reflux condenser was placed on the reaction flask. The reaction was allowed to stir for an additional 2.5 hours before being cooled to room temperature. The reaction was filtered and the remaining solids were washed with water. The isopropanol was then removed under reduced pressure and the remaining aqueous solution was acidified with concentrated hydrochloric acid to pH 2. This aqueous solution was extracted with dichloromethane (3x). The organic layers were collected, dried using magnesium sulfate and concentrated under reduced pressure to give 1.75 grams (72% yield) of the desired acid A8 as a white foam. ¹H NMR (d₆-DMSO, 500 MHz): δ 11.91 (s, 1H), 2.65 (td, J = 14.4, 6.4 Hz, 1H), 2.56 - 2.45 (m, 4H), 2.30 - 1.89 (m, 10H), 1.64 (m, 1H), 1.43 (dq, J = 13.5, 4.5 Hz, 1H), 1.20 (s, 3H), 0.75 (s, 3H). ¹³C NMR (d₆-DMSO, 125 MHz): δ 217.0, 212.1, 208.2, 174.6, 55.9, 49.9, 49.5, 49.1, 47.9, 36.8, 35.7, 34.6, 29.5, 28.9, 28.7, 21.1, 20.1, 14.4. HRMS(ESI): m/z calc. for C₁₈H₂₄O₅Na [M+Na]⁺: 343.1521, found: 343.1519.