4-Toluenesulfonyl chloride → tert-butyl N-{2-[(4-methylbenzenesulfonyl)oxy]ethyl}carbamate

Participants

Reaction Steps

To a mixture of tert-butyl 2-hydroxyethylcarbamate (6.4 g, 40 mmol) and Et3N (7.2 mL, 52 mmol) in DCM (50 mL) was added para-toluene sulfonylchloride, TsCl (8.4 g, 44 mmol). The mixture was stirred at room temperature (rt) overnight (ON). The reaction mixture was concentrated and the residue was partitioned between EA and water. The organic layer was separated, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography (PE/EA=5/1) to give 2-(tert-butoxycarbonylamino)ethyl 4-methylbenzenesulfonate (10.0 g, 79%) as white solid.

Provenance & Evidence