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

HRID 1650829
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1650829
[N+:1]([C:4]1[CH:58]=[CH:57][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:14][C@H:13]2[CH2:37][N:38]2[CH2:43][CH2:42][N:41]([C:44]([O:46][CH2:47][C:48]3[CH:53]=[CH:52][C:51]([N+:54]([O-:56])=[O:55])=[CH:50][CH:49]=3)=[O:45])[CH2:40][CH2:39]2)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].SCCO>FC(F)(F)C(O)=O.C1(C)C=CC=CC=1.C(OCC)(=O)C>[SH:17][C@@H:15]1[CH2:16][N:12]([C:10]([O:9][CH2:8][C:7]2[CH:57]=[CH:58][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[O:11])[C@H:13]([CH2:37][N:38]2[CH2:39][CH2:40][N:41]([C:44]([O:46][CH2:47][C:48]3[CH:49]=[CH:50][C:51]([N+:54]([O-:56])=[O:55])=[CH:52][CH:53]=3)=[O:45])[CH2:42][CH2:43]2)[CH2:14]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 15672-MercaptoethanolHCID 15056128(2S,4S)-1-(4-nitrobenzyloxycarbonyl)-2-[4-(4-nitrobenzyloxycarbonyl)piperazin-1-yl]methyl-4-(triphenylmethylthio)pyrrolidine

Produkt 1

HCID 15056064(2S,4S)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)-2-[4-(4-nitrobenzyloxycarbonyl)-piperazin-1-yl]methylpyrrolidineAusbeute 48,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140
Toluene
Lösungsmittel
HCID 6422Trifluoroacetic acidLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-673dbd217f094e4caa7bfb1a4d7ceb3c
Quelldatensatz
uspto-grants-1990_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04925838

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