Potassium Carbonate → HCID 57857006, compound

Participants

Reaction Steps

A mixture consisting of (3aR,4R,5R,6aS)-4-((R,E)-3-(benzo[b]thiophen-2-yl)-3-hydroxyprop-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate (intermediate 28, 0.343 g, 0.672 mmol) and potassium carbonate (0.046 g, 0.336 mmol), and 1:1 methanol-THF (12 mL) was stirred at room temperature for 18 hours. The reaction mixture turned from colorless to red-orange. After complete consumption of starting material, as judged by TLC, the reaction mixture was diluted with ethyl acetate (300 mL), washed with 1:1 saturated ammonium chloride-water (2×50 mL) and brine (50 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated to give a yellow solid. The material was triturated in 10% ethyl acetate in hexanes (200 mL) for three days. The product was collected to give an off-white solid which was rinsed with hexanes and dried to afford the title intermediate 29 (189 mg, 85% triturated yield) as an off-white solid; MS (ESI+) m/z 313 (m+H—H2O), (ESI−) m/z 389 (m+AcO−); 1H NMR (d6-DMSO) δ 7.83-7.93 (m, 1H), 7.72-7.83 (m, 1H), 7.24-7.38 (m, 2H), 7.19-7.24 (s, 1H), 5.94-6.01 (m, 1H), 5.65-5.82 (m, 2H), 5.31-5.38 (m, 1H), 4.94-5.01 (m, 1H), 4.84-4.93 (m, 1H), 3.80-3.91 (m, 1H), 2.74-2.88 (m, 1H), 2.56-2.69 (m, 1H), 2.22-2.37 (m, 3H), 1.64-1.80 (m, 1H).

Provenance & Evidence