The mixture from Example 9F (280 mg, 0.45 mmol), sodium methoxide (49.5 mg, 0.91 mmol) in methanol (10 mL) was refluxed for 12 hours. The mixture was acidified with 0.1 N aqueous hydrochloric acid to a pH around 5. The reaction mixture was partitioned with the addition of dichloromethane. The dichloromethane was collected and the aqueous solution was washed with dichloromethane (three times). The dichloromethane fractions were combined, dried and concentrated. The crude product was purified by preparative HPLC (Column: Phenomenex 150*30 mm; mobile phase: from 30% acetonitrile in H2O (0.01% TFA) to 70% acetonitrile in H2O (0.01% TFA) followed by chiral SFC purification (SFC condition: Column: AD-5 μm; Mobile phase:A, supercritical CO2; B, ethanol with 0.05% diethylamine, A:B=70:30 with a flow rate of 50 mL/min)) to give the title compound (peak 1 retention time: 5.58 minutes) and Example 10. 1H NMR (400 MHz, CD3OD) δ (ppm): 8.24 (d, J=5.2 Hz, 1H), 7.80 (m, 2H), 7.28 (m, 2H), 6.78 (m, 2H), 5.10 (m, 2H) 3.30-3.79 (m, 6H), 3.20 (m, 1H), 2.70-2.96 (m, 3H), 2.25-2.65 (m, 1H), 1.50-2.15 (m, 15H), 1.38 (m, 1H); MS (ESI+) m/z 583 (M+H)+.
