ethyl N-carbonylcarbamate → HCID 178498448, compound

To a suspension of methyl 3-aminocrotonate (2.0 g) in diethyl ether (15 mL) was added a solution of ethoxycarbonylisocyanate (2 g) in diethyl ether (5 mL) in a dropwise manner under ice-cooling, and the mixture was stirred at the same temperature for 4 hours. The insoluble material was collected by filtration, and the collected material was washed with diethyl ether, and dried under reduced pressure. To this material was added 25% aqueous triethylamine solution (20 mL), and the mixture was stirred at 50° C. overnight, and then stirred at 60° C. for 4 hours. The reaction mixture was concentrated under reduced pressure. The residual crystals were suspended in methylene chloride, and collected by filtration. The collected crystals were washed with methylene chloride, and dried under reduced pressure to give the title compound (1.59 g).

1. temperaturecooling
2. filtrationThe insoluble material was collected by filtration
3. washthe collected material was washed with diethyl ether
4. customdried under reduced pressure
5. additionTo this material was added 25% aqueous triethylamine solution (20 mL)
6. stirringthe mixture was stirred at 50° C. overnight
7. stirringstirred at 60° C. for 4 hours
8. concentrationThe reaction mixture was concentrated under reduced pressure
9. filtrationcollected by filtration
10. washThe collected crystals were washed with methylene chloride
11. customdried under reduced pressure

ORD record

ord-426459f5206547db97ef8229150f097e

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08217069B2