Isopropanol → HCID 86696603, compound

196 g (2.00 mol) of maleic anhydride was dissolved in 123 g (2.05 mol) of 2-propanol and 800 mL of ethyl acetate. Thereafter, 300 mL (2.15 mol) of triethylamine was added dropwise to the solution at an internal temperature of 10° C. or lower over 1.5 hours, and the obtained mixture was then stirred for 1 hour. Thereafter, 193 mL (2.03 mol) of ethyl chloroformate was added dropwise to the reaction mixture at an internal temperature of −5° C. or lower over 2 hours. After the mixture had been stirred for 30 minutes, the obtained reaction mixture was added dropwise to an aqueous solution containing 300 mL (2.16 mol) of 28% ammonia water and 250 g of ice. The obtained reaction mixture was left at room temperature overnight. Thereafter, 400 mL of ethyl acetate was added to reaction product, followed by stirring. Thereafter a liquid separation operation was performed on the reaction solution, so as to remove an aqueous layer. This operation was repeated three times. The obtained organic layers were gathered and were then concentrated. Recrystallized from hexane/ethyl acetate was performed, so as to obtain 50.5 g of isopropyl-(Z)-4-amino-4-oxo-2-butenoate in the form of a white solid. Yield: 16.1%.

1. stirringAfter the mixture had been stirred for 30 minutes
2. customthe obtained reaction mixture
3. additionwas added dropwise to an aqueous solution
4. customThe obtained reaction mixture
5. waitwas left at room temperature overnight
6. stirringby stirring
7. customThereafter a liquid separation operation
8. customso as to remove an aqueous layer
9. concentrationwere then concentrated
10. customRecrystallized from hexane/ethyl acetate

ORD record

ord-e9b32101157f48789df965ef047db822

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181203B2