1,1'-Carbonyldiimidazole → (1R,2S)-ethyl 1-(1H-imidazole-1-carboxamido)-2-vinylcyclopropanecarboxylate

HRID 420030Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 420030
S(C1C=CC(C)=CC=1)(O)(=O)=O.[NH2:12][C@:13]1([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:15][C@H:14]1[CH:16]=[CH2:17].[CH:23]1[N:27]=[CH:26][N:25]([C:28](N2C=NC=C2)=[O:29])[CH:24]=1>C1COCC1>[N:25]1([C:28]([NH:12][C@:13]2([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:15][C@H:14]2[CH:16]=[CH2:17])=[O:29])[CH:24]=[CH:23][N:27]=[CH:26]1

Komponenten

4

Edukt 2

HCID 682631,1'-CarbonyldiimidazoleHCID 46737761(1R,2S)-ethyl 1-amino-2-vinylcyclopropanecarboxylate 4-methylbenzenesulfonate

Produkt 1

HCID 57816680(1R,2S)-ethyl 1-(1H-imidazole-1-carboxamido)-2-vinylcyclopropanecarboxylateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Under nitrogen, (1R,2S)-ethyl 1-amino-2-vinylcyclopropanecarboxylate tosylate salt (5 g, 1 eq.) and CDI (2.7 g, 1.1 eq.) were dissolved in THF (50 mL) containing TEA (2.3 mL, 1.1 eq.). The reaction mixture was then refluxed overnight. The solvent was removed under reduced pressure. The residue was dissolved in DCM, and washed twice with water. The organic layer was dried over sodium sulfate and then concentrated. The residue was purified by chromatography on silica gel to yield compound 33 as pale yellow oil in 70% yield.

Aufarbeitung

  1. temperatureThe reaction mixture was then refluxed overnight
  2. customThe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in DCM
  4. washwashed twice with water
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-5ca7aadb592c4176b12c7c960d840523
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093379B2

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