Water → HCID 46908671, compound

Participants

Reaction Steps

32.5 mg 21 was dissolved in 1 ml THF, to which at 0° C. was added 0.28 ml pyridine solution (0.5 M in THF) followed by 0.5 ml water. Upon stirring, 25.6 mg thiophene-2-sulfonyl chloride in 1 ml THF was added dropwise. Additional 0.28 ml pyridine solution was added. The resulting solution was stirred vigorously at 0° C. and slowly warmed to room temperature. After 4 hours, the organic solvent was removed. The aqueous portion was diluted with 10 ml water and acidified at 0° C. with NaHSO4 solution (0.5 M). The mixture was extracted with ethyl acetate. The organic phase was combined, washed with water and brine and dried over Na2SO4. After removal of Na2SO4, the organic phase was concentrated and the crude product was purified via flash chromatography (5 g silica gel, DCM/CH3OH=20:1) affording 31 mg (58.4%) grey solid. 1H NMR (400 MHz, CD3CN) δ 8.36 (d, J=8.4 Hz, 1H), 8.00 (d, J=8.5 Hz, 1H), 7.68 (dd, J=5.0, 1.3 Hz, 1H), 7.62 (ddd, J=8.3, 6.8, 1.2 Hz, 1H), 7.54 (m, 2H), 7.43 (dd, J=3.8, 1.3 Hz, 1H), 7.28 (d, J=7.9 Hz, 1H), 7.04 (dd, J=5.0, 3.8 Hz, 1H), 3.78 (s, 2H). LRMS (ES−) 378 (M−H)−; HRMS (ES−) m/z calculated for C16H12NO4S3 (M−H)− 377.9934, found 377.9937.

Provenance & Evidence