反应详情

To a solution of 370 mg (1.12 mmol) of tert-butyl (2S)-2-hydroxy-3-[(2-pyridinylsulfonyl)amino]propylcarbamate & tert-butyl (2R)-2-hydroxy-3-[(2-pyridinylsulfonyl)amino]propylcarbamate in 3.3 mL of anhydrous dioxane, 20 mL of a 4 N solution of hydrogen chloride in dioxane was added. The resulting solution was stirred for 60 min, during which time a white precipitate formed. The mixture was concentrated under reduced pressure and the resulting solid was dried under vacuum. A 54 mg (0.18mmol) sample of the residue was then added to a solution of 90 mg (0.2 mmol) of (1S)-1-[(5,6-dichloro-1H-benzimidazol-1-yl)methyl]-2,2-dimethylpropyl 4-nitrophenyl carbonate in 2 mL of dimethylformamide. Addition of 0.22 mL (1.12 mmol) of diisopropylethylamine resulted in a light yellow solution, which was stirred for 1 d under nitrogen, and then concentrated. The residue was then partition between ethyl acetate and a saturated aqueous sodium bicarbonate solution. The layers were separated and the organic phase was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel chromatography eluting with a methanol:chloroform solution (1:9) to afford 44 mg (45%) of (1S)-1-[(5,6-dichloro-1H-benzimidazol-1-yl)methyl]-2,2-dimethylpropyl (2S)-2-hydroxy-3-[(2-pyridinylsulfonyl)amino]propylcarbamate & (1s)-1-[(5,6-dichloro-1H-benzimidazol-1-yl)methyl]-2,2-dimethylpropyl (2R)-2-hydroxy-3-[(2-pyridinylsulfonyl)amino]propylcarbamate. ES-LCMS m/z 544 (M+H) retention time=3.60 min.

1. customformed
2. concentrationThe mixture was concentrated under reduced pressure
3. customthe resulting solid was dried under vacuum
4. customresulted in a light yellow solution, which
5. stirringwas stirred for 1 d under nitrogen
6. concentrationconcentrated
7. customThe residue was then partition between ethyl acetate
8. customThe layers were separated
9. dry with materialthe organic phase was dried over anhydrous magnesium sulfate
10. concentrationconcentrated
11. customThe residue was purified by silica gel chromatography
12. washeluting with a methanol