1,1'-Carbonyldiimidazole → Diisopropylethylamine

HRID 2289056Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2289056
CO[C:3]1[CH:31]=CC(CS[C@@H]2CN(C(OCC3C=CC([N+]([O-])=O)=CC=3)=O)[C@H](C(O)=O)C2)=C[CH:4]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.FC(F)(F)C(O)=O.[N+](C1C=CC(COC(N=C(NC(OCC2C=CC([N+]([O-])=O)=CC=2)=O)N[CH2:65][C:66]([NH:68][CH:69]2[CH2:72]N[CH2:70]2)=O)=O)=CC=1)([O-])=O>C(#N)C>[CH:3]([N:68]([CH2:66][CH3:65])[CH:69]([CH3:70])[CH3:72])([CH3:31])[CH3:4]

Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 15297071(2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-prolineHCID 178521335HCID 178521335, Verbindung

Produkt 1

HCID 81531Diisopropylethylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

To a solution of (2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-proline (1.43 g) in anhydrous acetonitrile (22 ml), N,N-carbonyldiimidazole (545 mg) was added. The resulting mixture was stirred at room temperature for 30 minutes. To the reaction mixture, N,N-diisopropylethylamine (581 μl) and a solution of the compound (2.78 g), which had been obtained in (2), in anhydrous acetonitrile (23 ml) were added and the mixture was stirred overnight at room temperature. To the reaction mixture, dichloromethane was added. The resulting mixture was washed with water and saturated saline, dried over anhydrous magnesium sulfate and then concentrated by evaporation under reduced pressure, whereby 2.57 g of the title compound were obtained as a colorless amorphous substance.

Quellen und Nachweise

ORD-Eintrag
ord-3e5b74a0250a45798417a6afc8e48f86
Quelldatensatz
uspto-grants-2000_07
Patentnummer
US06090802

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