反应详情

To 154 mg (0.31 mmol) of N-[(2S,3S)-3-amino-2-hydroxyheptyl]-2-pyridinesulfonamide hydrochloride & N-[(2R,3S)-3-amino-2-hydroxyheptyl]-2-pyridinesulfonamide in 3 mL of dimethylformamide, 132 mg (0.31 mmol) of (1S)-1-{[4-(1H-imidazol-1-yl)phenoxy]methyl}-2,2-dimethylpropyl 4-nitrophenyl carbonate was added, followed by 0.25 mL (1.43 mmol) of N,N-diisopropylethylamine. The reaction mixture was stirred for 18 h at room temperature. It was concentrated, a saturated sodium bicarbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel column chromatography eluting with an methanol:chloroform solution (1:9) to yield 101.3 mg (57%) of (1S)-1-{[4-(1H-imidazol-1-yl)phenoxy]methyl}-2,2-dimethylpropyl (1S)-1-{(1S)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate and (1S)-1-{[4-(1H-imidazol-1-yl)phenoxy]methyl}-2,2-dimethylpropyl (1S)-1-{(1R)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate. ES-LCMS m/z 574 (M+H) Rt=2.7 min.

1. concentrationIt was concentrated
2. additiona saturated sodium bicarbonate solution was added
3. extractionthe mixture was extracted with ethyl acetate
4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by silica gel column chromatography
9. washeluting with an methanol