Proton sponge → HCID 68713421, compound

Participants

Reaction Steps

4-[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-1-(methylamino)butan-2-ol-carbamic acid tert-butyl ester (75 mg, 0.161 mmol), trimethyloxonium tetrafluoroborate (71 mg, 0.483 mmol), proton sponge (121 mg, 0.564 mmol) and 4A molecular sieves were stirred in dichloromethane (5 mL) in a sealed vial at room temperature for 18 hr. The reaction mixture was concentrated then loaded directly onto silica gel and purified via Isco chromatography (Redisep, silica, gradient 0-50% ethyl acetate in hexane to afford 0.065 g of (2S)-4-[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-2-methoxy-N-methylbutan-1-amine-carbamic acid tert-butyl ester as a clear oil. This material was dissolved in diethyl ether and methanol and 4N HCl in dioxane was added a precipitate formed. The mixture was filtered to afford 0.050 g of (2S)-4-[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-2-methoxy-N-methylbutan-1-amine as a brown solid.

Provenance & Evidence