反应详情

To a solution of 40 mg (0.12 mmol) of tert-butyl (1S)-1-{(1S)-2-[(6-fluoro-2-pyridinyl)amino]-1-hydroxyethyl}pentylcarbamate & tert-butyl (1S)-1-{(1R)-2-[(6-fluoro-2-pyridinyl)amino]-1-hydroxyethyl}pentylcarbamate in 1 mL dioxane was added 5 mL of 4M hydrochloric acid in dioxane. The reaction mixture was stirred for 2 h before being concentrated under reduced pressure. The residue was dissolved in 1 mL of N,N-dimethylformamide before 0.081 mL (0.47 mmol) of N,N-diisopropylethylamine and 56 mg (0.12 mmol) of (1S)-2,2-dimethyl-1-({3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)propyl 4-nitrophenyl carbonate were added. The reaction mixture was stirred at room temperature for 18 h, diluted with ethyl acetate, washed with 1M sodium hydroxide and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with ethyl acetate:hexanes (2:3) to afford 40 mg (59%) of (1S)-2,2-dimethyl-1-({3-[4(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)propyl (1S)-1-{(1S)-2-[(6-fluoro-2-pyridinyl)amino]-1-hydroxyethyl}pentylcarbamate & (1S)-2,2-dimethyl-1-({3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)propyl (1S)-1-{(1R)-2-[(6-fluoro-2-pyridinyl)amino]-1-hydroxyethyl}pentylcarbamate. ES-LCMS m/z 602 (M+Na).

1. concentrationbefore being concentrated under reduced pressure
2. additionwere added
3. stirringThe reaction mixture was stirred at room temperature for 18 h
4. washwashed with 1M sodium hydroxide and brine
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel chromatography
8. washeluting with ethyl acetate:hexanes (2:3)