2-Mercaptoethanol → (2S,4S)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)-2-[4-(4-nitrobenzyloxycarbonyl)-piperazin-1-yl]methylpyrrolidine

To a solution of (2S,4S)-1-(4-nitrobenzyloxycarbonyl)-2-[4-(4-nitrobenzyloxycarbonyl)piperazin-1-yl]methyl-4-(triphenylmethylthio)pyrrolidine (2.76 g) in trifluoroacetic acid (15 ml) was added 2-mercaptoethanol (0.31 ml) under ice-cooling and the mixture was stirred at ambient temperature for 10 minutes. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was dissolved in toluene (20 ml) and the solution was evaporated in vacuo to give a syrup. The syrup was dissolved in ethyl acetate (60 ml) and washed successively with saturated aqueous sodium hydrogen carbonate (30 ml) and saturated aqueous sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure 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)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)-2-[4-(4-nitrobenzyloxycarbonyl)-piperazin-1-yl]methylpyrrolidine (0.93 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. customto give a syrup
6. washwashed successively with saturated aqueous sodium hydrogen carbonate (30 ml) and saturated aqueous sodium chloride
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated under reduced pressure
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

ORDレコード

ord-1e0ecc1aa0de44c1b9924e204437da6f

出典データセット

uspto-grants-1993_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05202437