Triethylamine → tert-butyl 3-chloro-5-((3,5-dichloro-2-hydroxy-N-isobutylphenylsulfonamido)methyl)benzyl(isobutyl)carbamate

Participants

Reaction Steps

To a solution of tert-butyl 3-chloro-5-((isobutylamino)methyl)benzyl(isobutyl)carbamate (2.4 g, 6.27 mmol) in CH2Cl2 (30 mL) was added Et3N (1.3 mL, 9.40 mmol), followed by the addition of 3,5-dichloro-2-hydroxybenzenesulfonyl chloride (1.80 g, 6.89 mmol). The reaction mixture was stirred at rt for 2 h. The mixture was diluted with CH2Cl2 and water. The organic layer was washed with saturated NaHCO3 solution, NH4Cl solution, brine solution, and dried over MgSO4. The filtrate was concentrated and the residue was purified by silica gel flash chromatography. The column was eluted with hexane to 80% dichloromethane in hexane. The fractions containing the desired product were combined and concentrated to give colorless viscous solid (2.8 g, 72%).

Provenance & Evidence