Hydrochloric Acid → HCID 44224066, compound

Participants

Reaction Steps

0.45 mL of BBr3 solution (1.18 g, 4.73 mmol) was added dropwise into a solution of compound 8 (310 mg, 0.40 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 1 h at room temperature. The aqueous layer was extracted with dichloromethane (3×50 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 (H2O/Acetonitrile) to give 200 mg of compound 10 (72%) as white-yellow solid. 1H NMR (600 MHz, CD3OD) δ 7.56 (d, J=6.6 Hz, 2H), 7.39 (t, J1=6.0 Hz, J2=3.0 Hz, 4H), 7.35 (t, J1=6.0 Hz, J2=6.6 Hz, 4H), 7.23 (t, J1=6.0 Hz, J2=6.6 Hz, 2H), 7.06 (s, 1H), 6.99 (s, 1H), 3.76 (dd, J1=6.6 Hz, J2=11.4 Hz, 1H), 3.68 (m, 3H), 3.22 (m, 2H), 1.90 (s, 3H), 1.89 (s, 3H), 1.43 (m, 6H). HRMS calcd for C42H40N2O8 701.2857 (M+H), found 701.2853. 150 mg of compound 10 was further purified using a CHIRALCEL OD-RH 5 μM 250 mm×10 mm reverse phase chiral column to give 50 mg of compound 13 and 58 mg of compound 14, respectively.

Provenance & Evidence