Hydrochloric Acid → HCID 9816448, compound

Temperature

90 °C

A mixture of methyl N-[(S)-1-(4-methoxyphenyl)ethyl)-(S)-3-amino-3-(3-pyridyl)propanoate (57.35 g, 0.148 mol) and triethylsilane (25.81 g, 0.222 mol) in formic acid (120 mL) was heated to 90° C. (oil-bath) while stirring. The initial suspension became a clear solution after 5 minutes at 90° C. Heating and stirring was continued for 2 h. The reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure at 50° C. to give a residual oil. The residual oil was dissolved in ethyl acetate (300 mL) and methanol (100 mL). The solution was filtered. The filtrate was treated slowly with 9.8 M HCl in methanol (30.2 mL, 0.296 mol) with stirring. The resulting solution was diluted with ethyl acetate (200 mL) and heated on a steam-bath to remove excess methanol until the solution became cloudy. The mixture was then stirred at room temperature overnight and the solid product crystallized from the solution. Ethyl acetate (150 mL) was added to the suspension and the mixture was stirred for another 2 h. The solid was collected by filtration and washed with 200 mL of ethyl acetate, then dried in vacu for 1 h. The desired product was obtained as a white powder (27.05 g, 72% yield).

1. customafter 5 minutes
2. customat 90° C
3. temperatureHeating
4. stirringstirring
5. temperatureThe reaction mixture was cooled to room temperature
6. customthe solvent was removed under reduced pressure at 50° C.
7. customto give a residual oil
8. filtrationThe solution was filtered
9. stirringwith stirring
10. temperatureheated on a steam-bath
11. customto remove excess methanol until the solution
12. stirringThe mixture was then stirred at room temperature overnight
13. customthe solid product crystallized from the solution
14. additionEthyl acetate (150 mL) was added to the suspension
15. stirringthe mixture was stirred for another 2 h
16. filtrationThe solid was collected by filtration
17. washwashed with 200 mL of ethyl acetate
18. customdried in vacu for 1 h

ORD record

ord-e2d23c4c6f104ebda84b05bf0815073f

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06258956B1