Dichloromethane → 4-Chloro-N-(5-isopropyl-2-oxo-azepan-3-yl)-benzenesulfonamide

Participants

Reaction Steps

3-Azido-5-isopropyl-azepan-2-one (70 mg, 0.36 mmol) was dissolved in ethanol/water (2:1 v/v) and hydrogenated over 10% Pd-c (5 mg) for 2 h. The reaction mixture was filtered and concentrated under reduced pressure. The residue was taken up in dry CH2Cl2 (5 ml) and Hünig's base (0.09 ml, 0.54 mmol) was added and this mixture was cooled (ice-bath) followed by the dropwise addition of 4-chlorobenzylsulfonyl chloride (90.3 mg, 0.43 mmol) in CH2Cl2 (0.5 ml). The reaction mixture was stirred at r.t. for 1 h and then diluted with CH2Cl2 and washed with NaHCO3 (1/2 sat., 3×), 5% KHSO4/10% K2SO4 (3×), water, brine, dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure and the crude product was purified over silica gel (ethyl acetate/n-heptane 1:2 to 1:1): white solid 0.08 g (75%); MS: m/e=343.0 (MH−)

Provenance & Evidence