Benzenesulfonyl chloride → HCID 59784109, compound

Participants

Reaction Steps

Intermediate 7 (200 mg, 0.37 mmol) is dissolved in dry CH2Cl2 (4 mL) and the flask sealed under N2. DIEA (96 μL, 0.56 mmol) is added, followed by benzenesulfonyl chloride (46 μL, 0.36 mmol), then the mixture stirred at RT for 2 h. The reaction is subsequently diluted with CH2Cl2 (50 mL) and washed with sat. NaHCO3 (50 mL), brine (50 mL) and dried (Na2SO4). After filtration, the solvent is removed under reduced pressure to afford an oil which is purified by flash chromatography on silica gel (25% Et2O/CH2Cl2). The title compound is isolated as a colourless glass (216 mg, 86% yield): 1H NMR δ (CDCl3) 7.51-7.86 (m, 5H), 7.03-7.25 (m, 4H), 6.69 (v br s, 1H), 6.04 (br d, J=8.2 Hz, 1H), 5.16-5.25 (m, 1H), 4.29-4.75 (br m, 3H), 3.47-4.21 (br m, 3H), 2.69-2.88 (br m, 5H), 2.38-2.67 (m, 2H), 1.81-2.09 (m, 5H), 1.55 (s, 3H), 1.46 (s, 9H), 1.23-1.31 (br m, 2H), 0.84-0.92 (br m, 3H), 0.76 (d, J=6.7 Hz, 2H); LCMS (APCl+) 685.6 (MH+, 100%).

Provenance & Evidence