Hydroxylamine → cis-N-hydroxy-6-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclohex-3-ene-1-carboxamide

Participants

Reaction Steps

To a solution of 181.0 mg (0.4 mmol) of cis-6-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclohex-3-ene-1-carboxylic acid and 162.2 mg (1.2 mmol) of 1-hydroxybenzotriazole in 3 mL of N,N-dimethylformamide at 0° C. was added 230.0 mg (1.2 mmol) of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride. The reaction mixture was stirred at room temperature for 1.5 h. To the reaction mixture at 0° C. was added 0.2 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) and dried over sodium sulfate. After removal of the ethyl acetate, the residue was triturated with a 7:3 mixture of hexane:ethyl acetate to give 71.9 mg of cis-N-hydroxy-6-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclohex-3-ene-1-carboxamide as a solid in 38% yield. MS: 468.1 (M+H)+

Provenance & Evidence