Beta-Alanine → N-(Benzylcarbamoyl)-beta-alanine

To a solution of β-alanine 5.0 g (56 mmol) in dichloromethane 56 ml and tetrahydrofuran 56 ml was added benzyl isocyanate 6.6 ml (53 mmol) at 0° C. After stirring at room temperature overnight, the reaction mixture was diluted with ethyl acetate 200 ml and washed with water 200 ml and brine 200 ml. The residual solution was concentrated to about 100 ml in vacuo. To the mixture was added 1N sodium hydroxide solution 60 ml at 0° C. The aqueous phase was acidified with 3N HCl aq. 20 ml and then extracted with ethyl acetate 100 ml twice. The extract was washed with brine 50 ml and dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo. To the residue was added ether:n-hexane=1:1 30 ml and the precipitate was corrected by filtration to obtain the title compound 7.05 g (59%).

1. washwashed with water 200 ml and brine 200 ml
2. concentrationThe residual solution was concentrated to about 100 ml in vacuo
3. additionTo the mixture was added 1N sodium hydroxide solution 60 ml at 0° C
4. extractionextracted with ethyl acetate 100 ml twice
5. washThe extract was washed with brine 50 ml
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationThe filtrate was concentrated in vacuo
9. additionTo the residue was added ether
10. filtrationn-hexane=1:1 30 ml and the precipitate was corrected by filtration

ORD record

ord-1bfefd1bd1064072947a53c11fb326a7

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040531B2