StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Sulfuric Acid → (2S,4R)-4-methanesulfonyloxy-1(4-nitrobenzyloxycarbonyl)-2-(2-oxoimidazolidin-1-yl)carbonylpyrrolidine

HRID 1590486
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1590486
P(Cl)(Cl)(Cl)=O.[CH3:6][S:7]([O:10][C@H:11]1[CH2:15][N:14]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)=[O:17])[C@H:13]([C:29]([OH:31])=O)[CH2:12]1)(=[O:9])=[O:8].[CH2:32]1[NH:37][C:35](=[O:36])[NH:34][CH2:33]1.S(=O)(=O)(O)O>O1CCCC1.O.C(OCC)(=O)C.CN(C)C=O>[CH3:6][S:7]([O:10][C@H:11]1[CH2:15][N:14]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)=[O:17])[C@H:13]([C:29]([N:34]2[CH2:33][CH2:32][NH:37][C:35]2=[O:36])=[O:31])[CH2:12]1)(=[O:8])=[O:9]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 1118Sulfuric AcidHCID 84532-ImidazolidinoneHCID 24813Phosphorus oxychlorideHCID 13502650trans-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)-L-proline

Produkt 1

HCID 15056143(2S,4R)-4-methanesulfonyloxy-1(4-nitrobenzyloxycarbonyl)-2-(2-oxoimidazolidin-1-yl)carbonylpyrrolidineAusbeute 84,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To a mixture of N,N-dimethylformamide (0.6 ml) and tetrahydrofuran (1.2 ml) was added dropwise phosphorus oxychloride (0.58 ml) at -5° C. and the mixture was stirred at 5° C. for 5 minutes. To the mixture was added a solution of (2S,4R)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)proline (2.0 g) in tetrahydrofuran (20 ml) under ice-cooling. The solution was stirred at the same temperature for 30 minutes. To a solution were added ethyleneurea (2.22 g) and conc. sulfuric acid (0.035 ml), and the mixture was stirred at 45°-50° C. for 3 hours. Ethyl acetate (100 ml) and water (40 ml) was poured into the reaction mixture. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and evaporated in vacuo to give a residue. The 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,4R)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)-2-(2-oxoimidazolidin-1-yl)carbonylpyrrolidine (1.98 g).

Aufarbeitung

  1. temperaturecooling
  2. stirringThe solution was stirred at the same temperature for 30 minutes
  3. stirringthe mixture was stirred at 45°-50° C. for 3 hours
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customto give a residue
  8. customThe residue was chromatographed on silica gel (100 g)
  9. washeluting with a mixture of chloroform and methanol (9:1, V/V)
  10. additionThe fractions containing the desired compound
  11. customwere collected
  12. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b61c3fb0761f4c9f9ab92904a0e20225
Quelldatensatz
uspto-grants-1993_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05202437

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion