Hydroxylamine → HCID 86607871, compound

Participants

Reaction Steps

To a solution of 152 mg (0.24 mmol) of cis-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]-1-(methylsulfonyl)pyrrolidine-3-carboxylic acid and 97.3 mg (0.72 mmol) of 1-hydroxybenzotriazole in 3 mL of N,N-dimethylformamide at 0° C. was added 138 mg (0.72 mmol) of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride. The reaction mixture was stirred at room temperature for 1.5 h. To the 0° C. reaction mixture was added 0.12 mL of 50% hydroxylamine solution. The resulting reaction mixture was stirred at room temperature for 18 h. The volatile materials were removed under reduced pressure below 40° C. The residue was dissolved in 80 mL of ethyl acetate. The organic layer was washed with a saturated sodium bicarbonate solution (5×30 mL) and a saturated sodium chloride solution (2×30 mL), dried over sodium sulfate and filtered. After removal of the ethyl acetate, the residue was triturated with a 7:3 hexane:ethyl acetate mixture to give 114.1 mg of cis-N-hydroxy-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]-1-(methylsulfonyl)pyrrolidine-3-carboxamide as a yellow solid in 89% yield. MS: 535.2 (M+H)+

Provenance & Evidence