Acetic Acid → (2S,4S)-4-mercapto-2-(1-methyl-1H-tetrazol-5-yl)thiomethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 346359Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 346359
C([S:9][C@@H:10]1[CH2:14][N:13]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[O:16])[C@H:12]([CH2:28][S:29][C:30]2[N:34]([CH3:35])[N:33]=[N:32][N:31]=2)[CH2:11]1)(=O)C1C=CC=CC=1.C[O-].[Na+].C(O)(=O)C>CO.C(OCC)(=O)C>[SH:9][C@@H:10]1[CH2:14][N:13]([C:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=2)=[O:16])[C@H:12]([CH2:28][S:29][C:30]2[N:34]([CH3:35])[N:33]=[N:32][N:31]=2)[CH2:11]1

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 18641564(2S,4S)-4-benzoylthio-2-(1-methyl-1H-tetrazol-5-yl)thiomethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Produkt 1

HCID 18641565(2S,4S)-4-mercapto-2-(1-methyl-1H-tetrazol-5-yl)thiomethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidineAusbeute 61,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (2S,4S)-4-benzoylthio-2-(1-methyl-1H-tetrazol-5-yl)thiomethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.60 g) in methanol (30 ml) was added sodium methoxide (28% solution in methanol) (0.78 ml) under ice-cooling. After stirring at the same temperature for 30 minutes, to this solution was added glacial acetic acid (1 ml). The mixture was concentrated under reduced pressure to give a residue. The residue was dissolved in ethyl acetate (100 ml). The solution was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (100 g) eluting with a mixture of dichloromethane and acetone (20:1, V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4S)-4-mercapto-2-(1-methyl-1H-tetrazol-5-yl)thiomethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (0.78 g).

Aufarbeitung

  1. temperaturecooling
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customto give a residue
  4. washThe solution was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customThe resulting residue was chromatographed on silica gel (100 g)
  8. washeluting with a mixture of dichloromethane and acetone (20:1, V/V)
  9. additionThe fractions containing the desired compound
  10. customwere collected
  11. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a6bdc3127ba54c9a890d32942a8ca759
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05061804

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