4-(4-Chlorophenoxy)benzene-1-sulfonyl chloride → N-(1-Benzyloxy-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-(R)-yl)-4-(4-chloro-phenoxy)-benzenesulfonamide

Participants

Reaction Steps

To a solution of 3.69 g of 3-(R)-amino-1-benzyloxy-1,3,4,7-tetrahydro-azepin-2-one from Step D in 30 mL of pyridine was added 6.28 g of 4-(4-chloro-phenoxy)-benzene sulfonyl chloride. The reaction was stirred at room temperature for 5 days. The reaction was extracted with ethyl acetate, and washed with 5% HCl (aq.) twice, NaHCO3 (aq.) twice, and NaCl (aq.) once. The aqueous layers were re-extracted with ethyl acetate, and the organic layers combined and dried over Na2SO4(s). The reaction mixture was filtered and the solvent removed. The mixture was dissolved in dichloromethane, and filtered over silica gel. The dichloromethane layer was discarded. The silica gel was eluted with ethyl acetate, and the solvent removed under vacuum. Next, ethyl ether was added, and the solids collected under vacuum. The solids were washed with ethyl ether, and dried. Obtained 4.59 g of a white solid. MS: 521 (M+Na), 499 (M+H).

Provenance & Evidence