Hydrochloric Acid → HCID 9931836, compound

Participants

Reaction Steps

cis-3-Benzyl-1-(4-methoxybenzenesulfonyl)-azepane-2-carboxylic acid (146 mg, 0.36 mmol) was dissolved in 4-mL of anhydrous methylene chloride. Dimethylformamide (10-μL) was added followed by oxalyl chloride (0.36-mL of a 2.0 M solution, 0.72 mmol). The reaction was allowed to stir at room temperature for 30 minutes. In a separate flask, 2.0-mL of tetrahydrofuran was used to suspend hydroxylamine hydrochloride (125 mg, 1.8 mmol). 0.2-mL of water was added to dissolve the mixture. The solution was cooled on ice then triethylamine (290 mg, 2.88 mmol) was added. This solution was stirred at 0° C. for 30 minutes. The acid chloride solution was then added and the reaction stirred at 0° C. for an additional 30 minutes. 20-mL of ethyl acetate was added followed by 20-mL of 0.25 M hydrochloric acid. The layers were separated and the aqueous phase was extracted with another 20-mL of ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate, filtered, and concentrated to leave a clear colorless oil which was chromatographed (silica gel, 0-1% methanol in methylene chloride) to afford the title compound ((M+H)+ 419.2, (M+NH4)+ 436.2).

Provenance & Evidence