Methanesulfonyl chloride → Ammonia

Participants

Reaction Steps

Methanesulphonyl chloride (15 μl, 0.19 mmol) was added to an ice-cooled solution of the title compound from example 64 (93 mg, 0.17 mmol) in pyridine (2 ml), and the reaction allowed to warm to room temperature, and stirred for 90 minutes. Tlc analysis showed starting material remaining, so additional methanesulphonyl chloride (15 μl, 0.19 mmol) was added, and the reaction stirred for a further hour. The reaction was quenched by the addition of aqueous ammonium chloride solution, and extracted with ethyl acetate. The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure. The residual solid was purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (90:10:1) as eluant, then repeated using dichloromethane:methanol:0.88 ammonia (95:5:1) to afford the title compound, 36 mg.

Provenance & Evidence