Methyl iodide → HCID 15056144, Verbindung

HRID 1650840Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1650840
[CH3:1][S:2]([O:5][C@H:6]1[CH2:10][N:9]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:12])[C@H:8]([CH2:24][N:25]2[CH2:29][CH2:28][NH:27][C:26]2=[O:30])[CH2:7]1)(=[O:4])=[O:3].[OH-].[Na+].I[CH3:34]>CN(C)C=O>[CH3:1][S:2]([O:5][C@H:6]1[CH2:10][N:9]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:12])[C@H:8]([CH2:24][N:25]2[CH2:29][CH2:28][N:27]([CH3:34])[C:26]2=[O:30])[CH2:7]1)(=[O:4])=[O:3]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 15056137HCID 15056137, Verbindung

Produkt 1

HCID 15056144HCID 15056144, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (2S,4R)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)-2-(2-oxoimidazolidin-1-yl)methylpyrrolidine (0.80 g) in N,N-dimethylformamide (10 ml) was added sodium hydroxide (78 mg) under ice-cooling and the mixture was stirred at the same temperature for 20 minutes. To a solution was added iodomethane (0.34 ml) and the mixture was stirred at 30° C.-50° C. for 1 hour. The reaction mixture was poured into ice-water (30 ml) and extracted twice with ethyl acetate (30 ml). The extract 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 chloroform and methanol (19:l,V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4R)-4-methanesulfonyloxy-2-(3-methyl-2-oxoimidazolidin-1-yl)methyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (0.78 g).

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred at 30° C.-50° C. for 1 hour
  3. extractionextracted twice with ethyl acetate (30 ml)
  4. washThe extract 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 chloroform and methanol (19:l,V/V)
  9. additionThe fractions containing the desired compound
  10. customwere collected
  11. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-eca514888a84474c9e949cd32775902a
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04925838

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