Hydrochloric Acid → HCID 44224066, compound

Participants

Reaction Steps

0.65 mL of BBr3 solution (1.72 g, 6.85 mmol) was added dropwise into a solution of compound 7 (420 mg, 0.55 mmol) in 20 mL of anhydrous CH2Cl2 at −78° C. Stirring was continued at −78° C. for 1 h, 0° C. for 1 h, and ambient temperature for 1 h. 50 grams of ice containing 10 mL of 6M HCl was added to the mixture and stirred for 30 min at room temperature. The aqueous layer was extracted with ethyl acetate (3×60 mL). The combined organic layer was washed with water, brine and dried over MgSO4. The solvent was concentrated in vacuo and the residue was purified using C-18 column chromatography followed by preparative HPLC (H2O/Acetonitrile) to give 150 mg of compound 9 (39%) as white-yellow solid. 1H NMR (600 MHz, CD3OD) δ 7.39 (d, J=4.2 Hz, 2H), 7.19 (m, 4H), 7.15 (t, J1=6.0 Hz, J2=6.0 Hz, 4H), 7.03 (t, J1=6.0 Hz, J2=6.0 Hz, 2H), 6.89 (s, 1H), 6.81 (s, 1H), 3.49 (m, 4H), 3.02 (m, 2H), 1.72 (s, 3H), 1.71 (s, 3H), 1.25 (s, 3H), 1.24 (s, 3H). HRMS calcd for C42H40N2O8 701.2857 (M+H), found 701.2865. 100 mg of compound 9 was further purified using a CHIRALCEL OD-RH 5 μM 250 mm×10 mm reverse phase chiral column to give 25 mg of compound 11 and 28 mg of compound 12, respectively.

Provenance & Evidence