Hydrochloric Acid → HCID 72189290, compound

Participants

Reaction Steps

A solution of Super-Hydride® (1 M in tetrahydrofuran, 0.388 mL, 0.388 mmol) was added slowly to a solution of methyl 5-(N-(4-ethylphenyl)-N-isobutylsulfamoyl)-2-(2-morpholinoacetyl)benzoate (65 mg, 0.129 mmol) in tetrahydrofuran (THF) (0.5 mL) at room temperature, under nitrogen. The solution was stirred for 16 hours, then treated with HCl (2 N, 2 mL) and stirred for 10 minutes. The mixture was basified with sodium bicarbonate solution and extracted with ethyl acetate (2×5 mL). The organics were dried (MgSO4) then evaporated and purification of the crude attempted on a silica (Si) cartridge eluting with 5% methanol-dichloromethane+0.5% ammonia, although this gave poor separation. Purification was successfully achieved using a silica (Si) cartridge eluting with 1-3% methanol-dichloromethane+0.1-0.3% ammonia to give the desired product as a cream solid, 31 mg. LCMS [LCMS1] Rt 0.90 min, m/z (ES+) 477 (M+H).

Provenance & Evidence