反应详情

To a solution of (2S,4S)-2-[(2S)-2-carbamoylpyrrolidin-1-yl]methyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine (1.76 g) in trifluoroacetic acid (10 ml) was added 2-mercaptoethanol (0.38 ml) under ice-cooling and the mixture was stirred at ambient temperature for 15 minutes. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was dissolved in toluene (10 ml) and the solution was evaporated in vacuo. The resulting residue was dissolved in ethyl acetate (50 ml), washed successively with saturated aqueous sodium hydrogen carbonate (20 ml) and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and evaporated in vacuo to give a residue. The residue was chromatographed on silica gel (100 g) eluting with a mixture of dichloromethane and acetone (9:1 V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4S)-2-[(2S)-2-carbamoylpyrrolidin-1-yl]methyl-4-mercapto-1-(4-nitrobenzyloxycarbonyl)-pyrrolidine (0.58 g).

1. temperaturecooling
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. customto give a residue
4. customthe solution was evaporated in vacuo
5. dissolutionThe resulting residue was dissolved in ethyl acetate (50 ml)
6. washwashed successively with saturated aqueous sodium hydrogen carbonate (20 ml) and saturated aqueous sodium chloride
7. dry with materialdried over anhydrous magnesium sulfate
8. customevaporated in vacuo
9. customto give a residue
10. customThe residue was chromatographed on silica gel (100 g)
11. washeluting with a mixture of dichloromethane and acetone (9:1 V/V)
12. additionThe fractions containing the desired compound
13. customwere collected
14. customevaporated in vacuo