Acetic Acid → HCID 15056141, Verbindung

HRID 1650837Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1650837
C([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C@H:7]([CH2:23][N:24]2[CH2:28][CH2:27][NH:26][C:25]2=[O:29])[CH2:6]1)(=O)C.C[O-].[Na+].C(O)(=O)C>CO>[SH:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C@H:7]([CH2:23][N:24]2[CH2:28][CH2:27][NH:26][C:25]2=[O:29])[CH2:6]1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 57168905(2S,4S)-4-acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-(2-oxoimidazolidin-1-yl)methylpyrrolidine

Produkt 1

HCID 15056141HCID 15056141, VerbindungAusbeute 69,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a solution of (2S,4S)-4-acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-(2-oxoimidazolidin-1-yl)methylpyrrolidine (1.22 g) in methanol (20 ml) was added 28% sodium methoxide in methanol solution (0.61 ml) on ice-bath under atmospheric pressure of nitrogen and the mixture was stirred at the same condition for 30 minutes. To a reaction mixture was added acetic acid (0.17 ml) and evaporated in vacuo. The resulting residue was dissolved in ethyl acetate (50 ml) and the solution was washed twice with saturated aqueous sodium chloride, dried over magnesium sulfate, and evaporated in vacuo. The resulting residue was chromatographed on silica gel (150 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)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)-2-(2-oxoimidazolidin-1-yl)methylpyrrolidine (0.76 g).

Aufarbeitung

  1. customevaporated in vacuo
  2. dissolutionThe resulting residue was dissolved in ethyl acetate (50 ml)
  3. washthe solution was washed twice with saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe resulting residue was chromatographed on silica gel (150 g)
  7. washeluting with a mixture of chloroform and methanol (9:1 V/V)
  8. additionThe fractions containing the desired compound
  9. customwere collected
  10. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c041ec51bc3141508fe1faff707de557
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04925838

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