Hydroxylamine → 3-[(4-but-2-ynoxyphenyl)sulfonylamino]-N-hydroxypropanamide

Participants

Reaction Steps

To N-{[4-(2-butynyloxy)phenyl]sulfonyl}-beta-alanine (0.80 g, 2.69 mmol) in dimethylformamide (5 mL) was added 1-hydroxybenzotriazole (0.436 g, 3.23 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (0.67 g, 3.5 mmol). After one hour 50% hydroxylamine in water (1.3 mL) was added. The reaction mixture was stirred overnight and concentrated in vacuo. Ethyl acetate was added and the organic phase washed with water (2×) and brine then dried over anhydrous sodium sulfate. Filtration and concentration in vacuo gave a white solid that was triturated with ethyl acetate to give 3-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)-N-hydroxypropanamide (0.30 g) as a white solid,. mp 118-128° C. Electrospray Mass Spec 313.3 (M+H)+.

Provenance & Evidence