Hydrochloric Acid → HCID 67150454, Verbindung

A mixture of (1R,2S)-2-(benzoylamino)cyclohexanecarboxylic acid (2.47 g, 10 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (2.30 g, 12 mmol), acetonitrile (25 ml) and tetrahydrofuran (25 ml) was stirred at room temperature for 30 min. The reaction mixture was concentrated under reduced pressure, methanol (25 ml) was added, and the mixture was stirred at 60° C. for 3 hrs. The reaction mixture was concentrated under reduced pressure, dil. hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The extract was washed with aqueous sodium hydrogen carbonate solution, then with saturated brine and dried (over anhydrous MgSO4). The solvent was evaporated under reduced pressure. 28% Sodium methoxide in methanol solution (1.93 g, 10 mmol) and methanol (30 ml) were added to the residue and the mixture was heated under reflux for 5 hrs. 1N Hydrochloric acid (11 ml) was added under ice-cooling, and methanol was evaporated under reduced pressure. Aqueous sodium hydrogen carbonate solution was added to the obtained residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried (over anhydrous MgSO4), and the solvent was evaporated under reduced pressure. The obtained solid was collected by filtration and washed with diisopropy ether to give methyl (1S,2S)-2-(benzoylamino)cyclohexanecarboxylate (1.33 g, 51%) as a colorless powder.

1. concentrationThe reaction mixture was concentrated under reduced pressure, methanol (25 ml)
2. additionwas added
3. stirringthe mixture was stirred at 60° C. for 3 hrs
4. concentrationThe reaction mixture was concentrated under reduced pressure, dil. hydrochloric acid
5. additionwas added
6. extractionthe mixture was extracted with ethyl acetate
7. washThe extract was washed with aqueous sodium hydrogen carbonate solution
8. dry with materialwith saturated brine and dried (over anhydrous MgSO4)
9. customThe solvent was evaporated under reduced pressure
10. temperaturethe mixture was heated
11. temperatureunder reflux for 5 hrs
12. temperaturecooling
13. custommethanol was evaporated under reduced pressure
14. additionAqueous sodium hydrogen carbonate solution was added to the obtained residue
15. extractionthe mixture was extracted with ethyl acetate
16. washThe extract was washed with saturated brine
17. dry with materialdried (over anhydrous MgSO4)
18. customthe solvent was evaporated under reduced pressure
19. filtrationThe obtained solid was collected by filtration
20. washwashed with diisopropy ether

ORD-Eintrag

ord-9adcb1b040fe457594be49dadbc1ab28

Quelldatensatz

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07943770B2