Triethylamine → HCID 86716487, compound

Temperature

20 °C

200.00 g (1.101 mol) of methyl 5-amino-4-oxopentanoate hydrochloride were initially charged in ethanol (3500 ml), 64.28 ml (1.321 mol) of hydrazine hydrate were added and the mixture was then heated at reflux for 45 min. After cooling, triethylamine (152 ml) was added and the mixture was evaporated to dryness. Water (500 ml) was added to the residue, and the mixture was concentrated. Ethanol (500 ml) was then added, the mixture was concentrated, and then toluene (500 ml) was added twice, followed in each case by evaporation to dryness. The residue (140 g) was dissolved in acetonitrile (500 ml) and, at 0° C., added dropwise to a solution of 307.85 g (1.784 mol) of (2-fluorophenyl)acetyl chloride (preparation: Journal of Organic Chemistry; 22; 1957; 879) and 304.86 ml (2.202 mol) of triethylamine in acetonitrile (1500 ml) and molecular sieve. The mixture was stirred at 20° C. for 3 days. The mixture was then filtered and the precipitate was washed with tert-butyl methyl ether and then dried. This gave 458 g of the target compound (90% of theory).

1. temperaturethe mixture was then heated
2. temperatureat reflux for 45 min
3. temperatureAfter cooling
4. customthe mixture was evaporated to dryness
5. additionWater (500 ml) was added to the residue
6. concentrationthe mixture was concentrated
7. additionEthanol (500 ml) was then added
8. concentrationthe mixture was concentrated
9. additiontoluene (500 ml) was added twice
10. customfollowed in each case by evaporation to dryness
11. dissolutionThe residue (140 g) was dissolved in acetonitrile (500 ml) and, at 0° C.
12. filtrationThe mixture was then filtered
13. washthe precipitate was washed with tert-butyl methyl ether
14. customdried

ORD record

ord-1e4a94b0ec9647169c4d31048d1a4707

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09150580B2