Hydrochloric Acid → HCID 135956077, compound

Participants

Reaction Steps

To a solution of compound 3 (8.72 g, 16.95 mmol) in THF (100 mL) was added a solution of 4 M HCl in dioxane (200 mL). The reaction mixture was stirred at rt and monitored with TLC and LC-MS. When all the starting material 3 was reacted, the reaction mixture was concentrated to dryness. 2-Thiophenesulfonyl chloride (3.10 g, 16.95 mmol) and dry dichloromethane (˜200 mL) were added to above residua. Triethylamine (12.0 mL, 86.1 mmol) was then slowly added to above mixture while cooling with an ice-water bath. The final mixture was stirred at rt overnight. It was then washed with brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated and purified with silica column chromatography eluting with dichloromethane-ethyl acetate (v/v 9/1), then hexanes-ethyl acetate (v/v 1/1). The product was recrystallized from hot methanol to give the title compound (23, 5.93 g) as light yellow solid in 62.4% yield. 1H NMR (CDCl3, 500 MHz) δ 10.48 (s, 1H), 8.45 (s, 1H), 8.41 (s, 1H), 7.67 (m, 2H), 7.61 (s, 1H), 7.58 (d, 2H, J=8.0 Hz), 7.50 (d, 2H, J=8.5 Hz), 7.14 (t, 1H, J=4.0 Hz), 7.07 (d, 1H, J=8.0 Hz), 6.94 (d, 1H, J=8.0 Hz), 4.66 (d, 1H, J=5.0 Hz), 4.07 (br d, 1H, J=13.5 Hz), 3.93 (s, 3H), 3.17 (t, 1H, J=13.0 Hz), 2.36 (m, 1H), 2.34 (s, 3H), 1.67-1.45 (m, 3H), 1.29 (m, 2H). LCMS (ESI) m/z 561.14 (MH+, 100); HPLC: tR=5.82 min.

Provenance & Evidence