反应详情

To a solution of (3S)-3-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.36 g) in methanol (5 ml) was added 28% sodium methoxide-methanol solution (0.97 ml) under ice-cooling and the mixture was stirred at the same temperature for 10 minutes. This solution was added to a solution of (2S, 4R)-4-t-butyldimethylsilyloxy-2-methanesulfonyloxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (2 g) in methanol (20 ml). The mixture was stirred at ambient temperature for 3 hours and then at 50°-60° C. for 5 hours. The reaction mixture was evaporated in vacuo to give a residue. The residue was dissolved in ethyl acetate (50 ml). The solution was washed with saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (100 g) eluting with a mixture of n-hexane and ethyl acetate (2:1 v/v). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S, 4R)-4-t-butyldimethylsilyloxy-1-(4 -nitrobenzyloxycarbonyl)-2-[{(3S)-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio}methyl]pyrrolidine (1.95 g).

1. temperaturecooling
2. stirringThe mixture was stirred at ambient temperature for 3 hours
3. waitat 50°-60° C. for 5 hours
4. customThe reaction mixture was evaporated in vacuo
5. customto give a residue
6. washThe solution was washed with saturated aqueous sodium chloride
7. dry with materialdried over magnesium sulfate
8. customevaporated in vacuo
9. customThe resulting residue was chromatographed on silica gel (100 g)
10. washeluting with a mixture of n-hexane and ethyl acetate (2:1 v/v)
11. additionThe fractions containing the desired compound
12. customwere collected
13. customevaporated in vacuo