Urea → HCID 22473514, compound

Temperature

75 °C

Polyphosphate ester (1.15 g, 3.89 mmol, 0.30 eq) was added to a sealed tube containing a solution of urea (1.17 g, 19.4 mmol), valeraldehyde (1.38 ml, 12.9 mmol) and acetoacetamide (1.31 g, 12.9 mmol) in THF (15 mL) under argon and heated at 75° C. for three hours. The reaction mixture was cooled to room temperature, polyphosphate ester (8.80 g, 29.8 mmol) was added and the reaction mixture was heated at 85° C. for four hours. The reaction mixture was cooled to room temperature and poured on ice. The aqueous solution was neutralized with 1N NaOH and extracted with chloroform (3×100 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated under vacuum to give the title compound (0.940 g, 97%): HRMS 192.1143 (M−H)−. The product was used in the next step without further purification.

1. temperatureThe reaction mixture was cooled to room temperature
2. temperaturethe reaction mixture was heated at 85° C. for four hours
3. temperatureThe reaction mixture was cooled to room temperature
4. additionpoured on ice
5. extractionextracted with chloroform (3×100 mL)
6. dry with materialThe combined organic layers were dried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated under vacuum

ORD record

ord-1340d4234aaa4c04bff56e05f0ea38e1

Source dataset

uspto-grants-2004_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06809102B2