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

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%).

1. washwashed with water 300 ml and brine 200 ml
2. extractionextracted with ethyl acetate 300 ml
3. washThe organic phase was washed with brine 200 ml
4. dry with materialdried with magnesium sulfate
5. filtrationfiltered
6. concentrationThe filtrate was concentrated in vacuo
7. customprecipitated by addition of ether 50 ml and n-hexane 150 ml

ORD record

ord-cc723e71f5f64b57a97a1dae070d8daa

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455488B2