Hydrochloric Acid → HCID 57467323, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl (1-(3-fluorobenzyl)-7-(3-(propylsulfonamido)propyl)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate (cf. 209 and 201a, 65 mg, 0.125 mmol) was dissolved in acetonitrile (800 μL) and methyl iodide (24 μL, 0.376 mmol) and cesium carbonate (0.102 g, 0.313 mmol) was added. The reaction mixture was heated for 24 hours in a sealed vessel to 80° C. The reaction mixture was diluted with ethyl acetate. The ethyl acetate solution was successively washed with water and saturated sodium chloride solution. The organic phase was dried (MgSO4) and concentrated in vacuo. The crude product was purified by preparative thin-layer chromatography (silica gel, dichloromethane, methanol). The obtained tert-butyl 1-(3-fluorobenzyl)-7-(3-(N-methylpropylsulfonamido)propyl)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate (65 mg, 0.122 mmol) was dissolved in 4 M hydrochloric acid in isopropanol and stirred at room temperature for 4 hours. The solvent was removed in vacuo. Diethyl ether was added and the precipitate removed by filtration and dried. Yield: 22 mg (0.047 mmol, 38%).

Provenance & Evidence