4-Toluenesulfonyl chloride → 4-Methyl-N-[(1S)-1-methyl-2-[[(4-methylphenyl)sulfonyl]oxy]ethyl]benzenesulfonamide

Participants

Reaction Steps

p-Toluenesulfonyl chloride (25.38 g, 133.1 mmol) was dissolved in 70 mL dry pyridine and cooled to 0° C. (S)-2-Aminopropan-1-ol (43, 5.0 g, 66 mmol) in 20 mL dry pyridine was added dropwise via an addition funnel and the resulting mixture was stirred for 20 h at RT. The reaction mixture was concentrated and the residue was partitioned between EtOAc and H2O. The organic layer was washed with 1N HCl (4×50 mL), H2O, 5% NaHCO3, brine, dried over MgSO4 and concentrated. The residue was purified by SiO2 chromatography (80% Hex:20% Acetone) to afford the title compound. MS (m/z): 384.2 (M+H) (Calc'd for C17H21NO5S2: 383.48).

Provenance & Evidence