反应详情

TiCl4 (1M in CH2Cl2, 12.6 mL, 12.6 mmol) was added to a solution of tetraisopropyl orthotitanate (1.24 mL, 4.2 mmol) in CH2Cl2 (80 mL) held at 0° C. under inert atmosphere. The mixture was stirred for 15 minutes, then (4S)-3-{[(4-methoxybenzyl)thio]acetyl}-4-phenyl-1,3-oxazolidin-2-one (6.0 g, 16.8 mmol) in dry CH2Cl2 (60 mL) was added dropwise over 30 minutes and the mixture was stirred for ten minutes. Then tert-butyl (4-{(E)-[(4-fluorophenyl)imino]methyl}phenoxy)acetate (11.1 g, 33.6 mmol) in dry CH2Cl2 (60 mL) was added dropwise over 30 minutes, the mixture was given −40° C. and stirred for 20 minutes. Ethyl diisopropyl amine (5.8 mL, 33.6 mmol) in 20 mL CH2Cl2 was added dropwise over 20 minutes and the mixture was stirred at −40° C. for 90 minutes. The mixture was then given −78° C., added isopropanol (50 mL) and slowly given room temperature over two hours. H2O (100 mL) was added and the mixture was stirred for 20 minutes at room temperature and then extracted twice with diethyl ether. The combined organic layer was washed with water, dried (MgSO4) and concentrated under reduced pressure. The crude product was dissolved in methanol and a precipitate formed. Filtration and drying the title compound.

1. customheld at 0° C. under inert atmosphere
2. stirringthe mixture was stirred for ten minutes
3. customwas given −40° C.
4. stirringstirred for 20 minutes
5. stirringthe mixture was stirred at −40° C. for 90 minutes
6. customwas then given −78° C.
7. stirringthe mixture was stirred for 20 minutes at room temperature
8. extractionextracted twice with diethyl ether
9. washThe combined organic layer was washed with water
10. dry with materialdried (MgSO4)
11. concentrationconcentrated under reduced pressure
12. dissolutionThe crude product was dissolved in methanol
13. customa precipitate formed
14. filtrationFiltration
15. dry with materialdrying the title compound