2-Chlorobenzenesulfonyl chloride → HCID 68552215, compound

Participants

Reaction Steps

To a solution of the amine from Step 13BE (100 mg, 0.43 mmol) in CH2Cl2 (2.9 mL) was added 2-chlorobenzenesulfonyl chloride (113 mg, 73 μl, 0.52 mmol) and sat. NaHCO3 (1.4 mL). The biphasic mixture was stirred at room temperature overnight. The reaction mixture was diluted with CH2Cl2 (3 mL) and poured into a Phase Separator cartridge. The organic phase was concentrated and purified by flash chromatography (elution with 0-20% EtOAc-hex). Lyophilization then afforded the title compound (121 mg), a white solid, in 70% yield. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.79 (d, J=13.6 Hz, 2H), 2.09-2.23 (m, 2H), 2.82-2.92 (m, 2H), 3.08 (t, J=11.9 Hz, 1H), 4.02 (d, J=12.4 Hz, 2H), 7.21-7.27 (m, 1H), 7.37-7.44 (m, 1H), 7.46-7.52 (m, 1H), 7.53-7.59 (m, 1H), 7.89 (dd, J=8.0, 1.6 Hz, 1H), 8.09 (d, J=6.3 Hz, 1 H), 8.73 (d, J=3.5 Hz, 1H). HRMS: calcd for C17H16ClF3N2O2S+H+, 405.06458. found (ESI-FTMS, [M+H]1+), 405.0652.

Provenance & Evidence