Thionyl Chloride → tert-butyl (4S)-1-methyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylate

HRID 1702200Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1702200
[CH3:1][N:2]1[CH2:6][C@@H:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[NH:4][C:3]1=[O:14].CC(C)([O-])C.[K+].[C:21]([S:29][CH2:30][C@H:31]([CH3:35])[C:32](Cl)=[O:33])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(SC[C@@H](C)C(O)=O)(=O)C1C=CC=CC=1.S(Cl)(Cl)=O>O1CCCC1.C(OCC)(=O)C>[CH3:1][N:2]1[CH2:6][C@@H:5]([C:7]([O:9][C:10]([CH3:11])([CH3:13])[CH3:12])=[O:8])[N:4]([C:32](=[O:33])[C@H:31]([CH3:35])[CH2:30][S:29][C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:3]1=[O:14]

Komponenten

8

Edukt 5

HCID 24386Thionyl Chloride2×HCID 12763916(S)-3-(benzoylthio)-2-methylpropionic acidHCID 12878434(2S)-3-benzoylthio-2-methylpropionyl chlorideHCID 13053976tert-Butyl (4S)-1-methyl-2-oxoimidazolidine-4-carboxylateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 13053985tert-butyl (4S)-1-methyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylateAusbeute 73,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

3.0 g of tert.-butyl (4S)-1-methyl-2-oxo-imidazolidine-4-carboxylate are dissolved in 20 ml of tetrahydrofuran. 1.7 g of potassium tert.-butoxide are added to the solution under cooling at about -30° C. and stirring, and the mixture is further stirred at the same temperature for 10 minutes. A solution of (2S)-3-benzoylthio-2-methylpropionyl chloride (prepared by heating the mixture of 3.4 g of (2S)-3-benzoylthio-2-methylpropionic acid and 10 ml of thionyl chloride at 50°-60° C. for 2 hours and then evaporating excess thionyl chloride under reduced pressure) in 10 ml of tetrahydrofuran is added dropwise to the mixture under ice-cooling and stirring. Then, said mixture is further stirred at room temperature overnight. After the reaction, the mixture is condensed under reduced pressure, and the residue is dissolved in ethyl acetate. The ethyl acetate solution is washed with water and an aquous sodium bicarbonate solution, dried and then evaporated to remove solvent. The oily residue thus obtained is purified by silica gel column chromatography (Solvent, toluene-ethyl acetate(20:1)). 4.5 g of tert-butyl (4S)-1-methyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylate are obtained as colorless crystals. Yield: 73.9% M.p. 128° C.

Aufarbeitung

  1. stirringthe mixture is further stirred at the same temperature for 10 minutes
  2. temperatureby heating
  3. temperaturecooling
  4. stirringstirring
  5. stirringis further stirred at room temperature overnight
  6. customAfter the reaction
  7. customcondensed under reduced pressure
  8. washThe ethyl acetate solution is washed with water
  9. dry with materialan aquous sodium bicarbonate solution, dried
  10. customevaporated
  11. customto remove solvent
  12. customThe oily residue thus obtained
  13. customis purified by silica gel column chromatography (Solvent, toluene-ethyl acetate(20:1))

Quellen und Nachweise

ORD-Eintrag
ord-35874e808ed4448faeaf1078f696bc5c
Quelldatensatz
uspto-grants-1983_04
Patentnummer
US04380644

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