Methanesulfonyl chloride → HCID 21084093, compound

Participants

Reaction Steps

Sodium bis(trimethylsilyl) amide (0.25 mL of a 1M solution in THF, 0.25 mmol) was added to a solution of the compound of Example 80 (105 mg, 0.25 mmol) in dry THF (5 mL) under a nitrogen atmosphere at 0°. After 30 min methane sulfonyl chloride (28.6 mg, 0.25 mmol) was added. The reaction mixture was allowed to warm to r.t. over 1 h then poured into saturated NaHCO3(aq) (20 mL) and the product extracted with DCM (2×20 mL). The combined organic fractions were dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by radial chromatography on silica (EtOAc) to give the title compound (115 mg, 92%). δH (CDCl3) 7.6–7.28 (11H, m), 6.55 (1H, d, J 9 Hz), 2.68 (3H, s), 1.32 (9H, s). m/z (ES+) 497 (M+H)+.

Provenance & Evidence