Triethylamine → HCID 86680473, compound

Participants

Reaction Steps

A solution of the product from Example 226A (0.14 g, 0.361 mmol) in dichloromethane (2.5 mL) and trifluoroacetic acid (2.5 mL) was stirred at room temperature for 2 hours and then concentrated in vacuo. The residue was dissolved in a mixture of dichloromethane (3 mL) and triethylamine (0.30 mL, 2.17 mmol), and 4-(trifluoromethyl)benzene-1-sulfonyl chloride (0.097 g, 0.398 mmol) was added. The resulting mixture was stirred at room temperature for 16 hours, and then it was partitioned between water and dichloromethane. The organic extract was dried over Na2SO4. The crude product was purified by column chromatography on silica gel using a solvent gradient of 0-3% ethyl acetate in heptane to give the title compound as a colorless solid (0.132 g, 74%). 1H NMR (300 MHz, CDCl3) δ ppm 1.72-1.90 (m, 1H) 1.91-2.06 (m, 1H) 2.06-2.20 (m, 1H) 2.33 (dd, J=9.49, 4.75 Hz, 1H) 2.37-2.70 (m, 3H) 3.00 (d, J=7.80 Hz, 1H) 3.58-3.73 (m, 1H) 3.77 (d, J=8.82 Hz, 1H) 3.92 (d, J=10.17 Hz, 1H) 5.41 (q, J=6.22 Hz, 1H) 6.79 (d, J=8.82 Hz, 1H) 7.76 (dd, J=8.65, 2.54 Hz, 1H) 7.79-7.94 (m, 4H) 8.39 (d, J=2.37 Hz, 1H); MS (ESI) m/z 496 (M+H)+.

Provenance & Evidence