Sulfuryl chloride → HCID 18436981, compound

Participants

Reaction Steps

The amine made above 11-2 (120 mg, 0.23 mmol) was dissolved in 5.0 mL of dry N,N-dimethylformamide and allowed to stir at ambient temperature. Then sulfonyl chloride (35 μL, 0.34 mmol) and diisopropylethylamine (125 μL, 0.72 mmol) were added via pipette, respectively. The reaction was stirred for 10 hours until completion via LCMS analysis. The crude reaction solution was partitioned between ethyl acetate (15 mL) and half-saturated NaHCO3 solution (100 mL). The layers were separated and the aqueous layer was extracted several times with ethyl acetate (3×10 mL). The combined organic layers were washed with water (4×15 mL), brine, separated, dried (Na2SO4) and concentrated in vacuo to afford a yellow oil. Chromatography (SiO2, 30% to 50% ethyl acetate in hexanes) followed by concentration afforded 11-3 as a pale yellow solid; 1H NMR (300 MM, CDCl3) δ 12.73 (s, 1 H), 8.25 (d, 1H, J=8.4 Hz), 7.93 (s, 1 H), 7.62 (d, 1 H, J=7.2 Hz), 7.61 (s, 1 H), 7.50 (m, 1 H), 7.40 (d, 1 H, J=8.1 Hz), 7.39 (d, 1 H, J=8.4 Hz), 7.24 (app t, 1 H, J=7.2 Hz), 6.69 (s, 1 H), 6.43 (dd, 1 H, J=16.5, 9.6 Hz), 6.26 (d, 1 H, J=16.5 Hz), 5.94 (d, 1 H, J=9.9 Hz), 4.82 (t, 1 H, J=5.1 Hz), 4.51 (s, 2 H), 3.25 (m, 4H), 1.43 (s, 9 H), 1.39 (s, 9 H).

Provenance & Evidence