Benzenesulfonyl chloride → (11S)-11-[(benzyloxy)methyl]-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-6-amine

A solution of (11S)-11-[(benzyloxy)methyl]-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinoline (3.7 g, 10 mmol) dissolved in CHCl3 was treated with mCPBA (50% purity, 4.8 g, 13 mmol). The reaction was stirred at ambient temperature for 18 hours. Saturated aqueous NaHCO3 (100 mL) and H2O (50 mL) were then added to the reaction and the layers were separated. The aqueous layer was extracted with additional CHCl3. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give a black oil. The oil was dissolved in methanol (53 mL) and treated with concentrated NH4OH solution (3.6 mL, 53 mmol). The solution was stirred and benzene sulfonyl chloride (2.9 mL, 53 mmol) was carefully added. The resulting reaction mixture was stirred at ambient temperature for 2 hours before adding additional concentrated NH4OH solution (3.6 mL, 53 mmol) and benzene sulfonyl chloride (2.9 mL, 53 mmol). Stirring was continued for 18 hours and then reaction mixture was concentrated under reduced pressure. The resulting material was treated with saturated aqueous NaHCO3 (50 mL) and H2O (50 mL), and then extracted with CHCl3. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to give a brown oil. The oil was treated with Et2O and the mixture was stirred until a precipitate formed. The solid was isolated by filtration to give 3.1 g of (11S)-11-[(benzyloxy)methyl]-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-6-amine as a tan solid.

1. customthe layers were separated
2. extractionThe aqueous layer was extracted with additional CHCl3
3. dry with materialThe combined organic layers were dried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure
6. customto give a black oil
7. stirringThe solution was stirred
8. customThe resulting reaction mixture
9. stirringwas stirred at ambient temperature for 2 hours
10. stirringStirring
11. waitwas continued for 18 hours
12. customreaction mixture
13. concentrationwas concentrated under reduced pressure
14. additionThe resulting material was treated with saturated aqueous NaHCO3 (50 mL) and H2O (50 mL)
15. extractionextracted with CHCl3
16. dry with materialThe organic layer was dried over Na2SO4
17. filtrationfiltered
18. concentrationconcentrated under reduced pressure
19. customto give a brown oil
20. stirringthe mixture was stirred until a precipitate
21. customformed
22. customThe solid was isolated by filtration

ORD 기록

ord-80eff1562d1246d3aa8325207155e7cd

출처 데이터셋

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08034938B2