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

To a solution of 2-(aminooxy)acetic acid (5 g, 46 mmol) and triethylamine (3.17 ml, 23 mmol) in dichloromethane (60 ml) and tetrahydrofuran (60 ml) was added benzyl isocyanate (5.43 ml, 44 mmol) and the mixture was 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 layer was washed with 1N-sodium hydroxide aq. (60 ml). The aqueous layer was acidified with 1N—HCl aq. (70 ml) and extracted with ethyl acetate (300 ml). The organic layer was washed with brine (200 ml), dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo and ether (50 ml) and n-hexane (150 ml) were added for precipitation to obtain the title compound (3.2 g, 33%).

1. washwashed with water (300 ml) and brine (200 ml)
2. washThe organic layer was washed with 1N-sodium hydroxide aq. (60 ml)
3. extractionextracted with ethyl acetate (300 ml)
4. washThe organic layer was washed with brine (200 ml)
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. concentrationThe filtrate was concentrated in vacuo and ether (50 ml) and n-hexane (150 ml)
8. additionwere added for precipitation

ORD record

ord-eab9c4120b504293851ad85d65acb4d6

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09126981B2