Methanesulfonyl chloride → HCID 18511975, compound

Participants

Reaction Steps

The crude product from Example 6C in pyridine (8.8 mL) was treated with methanesulfonyl chloride (0.28 mL, 3.60 mmoles) at 0° C. The reaction mixture turned from clear and colorless to yellow. After 30 minutes, the mixture was quenched with water (5.0 mL) and was concentrated under reduced pressure. The residue was dissolved in diethyl ether (200 mL), washed with water (2×100 mL), brine (100 mL), dried (Na2SO4), filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 4:1→1:1 hexanes:ethyl acetate) to provide the title compound as a yellow solid (1.33 g, 83%). A small portion of the residue (0.1 g) was repurified by preparative HPLC (CH3CN:0.1% TFA in H2O) on a YMC ODS Guardpak column. 1H NMR (300 MHz, CDCl3) δ7.92 (d, J=6.8 Hz, 2H), 7.21 (m, 8H), 7.11 (t, J=8.0 Hz, 1H), 6.89 (d, J=8.0 Hz, 1H), 6.11 (s, 1H), 4.12 (s, 2H), 4.05 (s, 2H), 3.90 (s, 3H), 2.95 (s, 3H), 2.34 (s, 3H); MS (APCI+) m/z 439 (M+H)+.

Provenance & Evidence