Hydrochloric Acid → HCID 86680463, compound

Participants

Reaction Steps

To a solution of the product from Example 206A (28 mg, 0.075 mmol) in 1,4-dioxane (1 mL) was added a 4 M solution of hydrogen chloride in 1,4-dioxane (0.5 mL, 2.0 mmol). The resulting mixture was stirred at room temperature for 90 minutes, and the mixture was then concentrated and dried in vacuo. To the resulting colorless solid was added CH2Cl2 (0.75 mL), diisopropylethylamine (0.065 mL, 0.375 mmol) and 3-(trifluoromethyl)benzene-1-sulfonyl chloride (22.02 mg, 0.090 mmol). The resulting mixture was stirred at room temperature for 3 hours. The mixture was partitioned between water and CH2Cl2, and the organic layer was dried over Na2SO4. The drying agent was removed by filtration, and the filtrate was concentrated in vacuo. The crude product was purified by column chromatography on silica gel using a solvent gradient of 0-40% ethyl acetate in hexanes. The title compound was obtained as a colorless solid (10 mg, 28%). 1H NMR (300 MHz, CDCl3) δ ppm 0.72-0.81 (m, 2H), 1.07-1.17 (m, 2H), 1.48 (s, 3H), 1.72-1.88 (m, 1H), 1.92-2.05 (m, 1H), 2.12 (t, J=10.51 Hz, 1H), 2.33 (dd, J=9.92, 5.16 Hz, 1H), 2.38-2.63 (m, 3H), 2.94-3.07 (m, 1H), 3.65 (dd, J=10.31, 6.74 Hz, 1H), 3.72-3.82 (m, 1H), 3.86-3.98 (m, 1H), 5.23-5.35 (m, 1H), 7.70 (t, J=7.93 Hz, 1H), 7.87 (d, J=7.93 Hz, 1H), 7.96 (d, J=7.93 Hz, 1H), 8.00 (d, J=1.19 Hz, 1H), 8.01-8.04 (m, 1H), 8.05 (d, J=1.19 Hz, 1H); MS (ESI) m/z 483 (M+H)+.

Provenance & Evidence