Hydrochloric Acid → HCID 66696644, compound

Participants

Reaction Steps

A solution of Example 51D (504 mg, 1.36 mmol) in THF (5 mL) was stirred at room temperature, followed by addition of 6N aq HCl (3.4 mL, 6.8 mmol). After 10 min water (20 mL) and CH2Cl2 (10 mL) were added and the layers separated. The aqueous layer was washed with CH2Cl2 (5 mL). The aqueous layer was then neutralized with saturated NaHCO3 solution and extracted with CH2Cl2 (3×20 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The residue was taken up in MeOH (5 mL) and K2CO3 (938 mg, 6.78 mmol) was added. After 20 min CH2Cl2 (50 mL) was added and the mixture was filtered and concentrated in vacuo. The crude product was purified by flash chromatography (50%-100% EtOAc/hexanes) to afford 145 mg (65%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 6.73 (t, J=8.0, 1H), 6.18 (dd, J=7.9, 1.1, 1H), 5.98 (dd, J=8.1, 1.0, 1H), 5.06 (d, J=4.2, 1H), 4.81 (bs, 2H), 4.01-3.92 (m, 2H), 3.63 (dd, J=11.0, 8.1, 1H), 2.64 (dd, J=16.9, 6.2, 1H), 2.23 (dd, J=16.1, 6.7, 1H). MS (ESI+) m/z 166 (M+H).

Provenance & Evidence