Dicyclohexylcarbodiimide → HCID 14278860, Verbindung

HRID 371804

Reaktionsgleichung

Reaktionsgleichung von HRID 371804
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:14]([OH:16])=O)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:18][O:19][C:20](=[O:27])[C@H:21]([CH2:23][CH:24]([CH3:26])[CH3:25])[NH2:22].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>C(N(CC)CC)C.CN(C)C=O>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:14]([NH:22][C@H:21]([C:20]([O:19][CH3:18])=[O:27])[CH2:23][CH:24]([CH3:26])[CH3:25])=[O:16])[CH3:13])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 70832N-Cbz-d-alanineHCID 757711-HydroxybenzotriazoleHCID 2723695Leucine methyl ester hydrochloride

Produkt 1

HCID 14278860HCID 14278860, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Nα -Benzyloxycarbonyl-D-alanyl-L-leucine, methyl ester is prepared by the following procedure. A solution of 8.92 g. of Nα -benzyloxycarbonyl-D-alanine, 7.28 g. of leucine methyl ester hydrochloride and 5.4 g. of 1-hydroxybenztriazole in 120 ml. of dimethylformamide is cooled to -10° C. with stirring and is treated with 5.6 ml. of triethylamine. The mixture is stirred for ten minutes at -10° C. and is treated with 8.6 g. of dicyclohexylcarbodiimide. The reaction is then stirred at -10° C. for fifteen minutes, brought to 0° C. and stirred to 10° during two hours following which it is stirred overnight at 20° C. The mixture is warmed to 50° C. and stirred for 2 hours.

Aufarbeitung

  1. additionis treated with 5.6 ml
  2. stirringThe mixture is stirred for ten minutes at -10° C.
  3. additionis treated with 8.6 g
  4. stirringThe reaction is then stirred at -10° C. for fifteen minutes
  5. custombrought to 0° C.
  6. stirringstirred to 10° during two hours
  7. stirringis stirred overnight at 20° C
  8. stirringstirred for 2 hours

Quellen und Nachweise

ORD-Eintrag
ord-31c9d3bb5edb4b3397f269ecae160b7c
Quelldatensatz
uspto-grants-1978_05
Patentnummer
US04087418

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