(Aminooxy)acetic acid → 2-((3-Benzylureido)oxy)acetic acid

Participants

Reaction Steps

To the solution of 2-(aminoxy)acetic acid 5 g (46 mmol) and triethylamine 3.17 ml (23 mmol) in dichloromethane 60 ml and tetrahydrofuran 60 ml, benzyl isocyanate 5.43 ml (44 mmol) was added and stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate 400 ml and washed with water 300 ml and brine 200 ml. The organic phase was basified with 1N-sodium hydride 60 ml. The aqueous phase was acidified with 1N-hydrochloric acid 70 ml and extracted with ethyl acetate 300 ml. The organic phase was washed with brine 200 ml and dried with magnesium sulfate and filtered. The filtrate was concentrated in vacuo and precipitated by addition of ether 50 ml and n-hexane 150 ml to obtain the title compound 3.2 g (33%).

Provenance & Evidence