2-Mercaptoethanol → (2S,4S)-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]methyl-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 1590495Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1590495
[OH:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][C@@H:9]1[CH2:13][C@H:12]([S:14]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:11][N:10]1[C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][C:41]([N+:44]([O-:46])=[O:45])=[CH:40][CH:39]=1)=[O:35].SCCO>FC(F)(F)C(O)=O.C(OCC)(=O)C>[OH:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][C@@H:9]1[CH2:13][C@H:12]([SH:14])[CH2:11][N:10]1[C:34]([O:36][CH2:37][C:38]1[CH:39]=[CH:40][C:41]([N+:44]([O-:46])=[O:45])=[CH:42][CH:43]=1)=[O:35]

Komponenten

5

Edukt 2

HCID 15672-MercaptoethanolHCID 15056147(2S,4S)-2-[(2S)-2-(hydroxymethyl)-pyrrolidin-1-yl]methyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine

Produkt 1

HCID 15056150(2S,4S)-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]methyl-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidineAusbeute 49,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6422Trifluoroacetic acidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (2S,4S)-2-[(2S)-2-(hydroxymethyl)-pyrrolidin-1-yl]methyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine (5.74 g) in trifluoroacetic acid (30 ml) was added 2-mercaptoethanol (0.95 ml) under ice-cooling and the mixture was stirred at ambient temperature for 15 minutes. The reaction mixture was evaporated in vacuo. The resulting residue was dissolved in toluene (30 ml) and the solution was evaporated in vacuo to give a residue. The residue was dissolved in ethyl acetate (100 ml) and the solution was washed in turn with saturated aqueous sodium hydrogen carbonate and 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 chloroform and methanol (9:1, V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4S)-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]methyl-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.77 g).

Aufarbeitung

  1. temperaturecooling
  2. customThe reaction mixture was evaporated in vacuo
  3. dissolutionThe resulting residue was dissolved in toluene (30 ml)
  4. customthe solution was evaporated in vacuo
  5. customto give a residue
  6. washthe solution was washed in turn with saturated aqueous sodium hydrogen carbonate and 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 chloroform and methanol (9:1, V/V)
  11. additionThe fractions containing the desired compound
  12. customwere collected
  13. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e57f99bb86f640d8befbeaf4768efa74
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05202437

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