反应详情

To a solution of 0.101 g (0.29 mmol) of tert-butyl (1S,2S)-2-hydroxy-1-methyl-3-[(2-pyridinylsulfonyl)amino]propylcarbamate & tert-butyl (1S,2R)-2-hydroxy-1-methyl-3-[(2-pyridinylsulfonyl)amino]propylcarbamate in 2 mL of dioxane was added 2.0 mL of a 4.0 M solution of hydrochloric acid in dioxane. The reaction mixture was stirred for 30 min, and then concentrated. This residue was dissolved in 3.0 mL of dimethylformamide and this solution was added to 0.14 g (0.29 mmol) of (1S)-2,2-dimethyl-1-({3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)propyl 4-(nitro)phenyl carbonate and 1.5 mL (0.87 mmol) of diisopropylethylamine. The reaction mixture was stirred at room temperature for 16 h. A saturated solution of sodium bicarbonate was then added, followed by diethyl ether. The layers were separated, and the organic layer was dried over anhydrous magnesium sulfate, and concentrated under vacuum to afford the crude product. This crude product was purified via silica gel chromatography eluting with ethyl acetate:hexane (1:1) to afford 0.138 g (81%) of (1S)-2,2-dimethyl-1-({3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)propyl (1S,2S)-2-hydroxy-1-methyl-3-[(2-pyridinylsulfonyl)amino]propylcarbamate & (1S)-2,2-dimethyl-1-({3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)propyl (1S,2R)-2-hydroxy-1-methyl-3-[(2-pyridinylsulfonyl)amino]propylcarbamate as a colorless oil. 1H-NMR (300 MHz, CDCl3): δ 8.64 (m, 1H), 7.98–7.88 (m, 5H), 7.64–7.47 (m, 4H), 6.60 (s, 1H), 5.01–4.81 (m, 3H), 4.46, 4.42 (2s br, 1H), 4.25–4.17 (m, 2H), 3.59–3.44 (m, 2H), 3.14 (m, 1H), 1.00 (m, 12H); LC-MS 584 (M+H).

1. concentrationconcentrated
2. dissolutionThis residue was dissolved in 3.0 mL of dimethylformamide
3. stirringThe reaction mixture was stirred at room temperature for 16 h
4. customThe layers were separated
5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
6. concentrationconcentrated under vacuum
7. customto afford the crude product
8. customThis crude product was purified via silica gel chromatography
9. washeluting with ethyl acetate:hexane (1:1)