Dicyclohexylcarbodiimide → HCID 178512917, Verbindung

HRID 638794Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 638794
C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.Cl.[CH2:21]([O:28][C:29]([NH:31][C@H:32]([C:40]([OH:42])=[O:41])[CH2:33][CH2:34][CH2:35][NH:36][C:37](=[NH:39])[NH2:38])=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[NH:31]([C:29]([O:28][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:30])[C@H:32]([C:40]([OH:42])=[O:41])[CH2:33][CH2:34][CH2:35][NH:36][C:37](=[NH:38])[NH2:39]

Komponenten

6

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 178479461HCID 178479461, Verbindung

Produkt 1

HCID 178512917HCID 178512917, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The amino-component (10 mmol) was dissolved in DMF (70 ml), and 4.59 g (30 mmol monohydrate) HOBT was added. To the solution was diisopropyletylamine (DIPEA) added dropwise, until the pH of the mixture, controlled with wet indicator paper reached 7-8. Next, the N-benzyloxycarbonyl-arginine hydrochloride (5.17 g, 15 mmol) was added and the solution was cooled on ice bath. N,N′-Dicyclohexylcarbodiimide (3.09 g, 15 mmol) was added in small portions during 1 h. and after additional 1 h of stirring, the reaction mixture was left in a cold room overnight (approximately 4° C.). The precipitated DCU was filtered off and washed with a small volume of DMF and the combined filtrates were evaporated under reduced pressure. From the resulting mixture cystapep 1 (or its analogues) was isolated using chromatography techniques.

Aufarbeitung

  1. additionadded dropwise, until the pH of the mixture
  2. temperaturethe solution was cooled on ice bath
  3. filtrationThe precipitated DCU was filtered off
  4. washwashed with a small volume of DMF
  5. customthe combined filtrates were evaporated under reduced pressure
  6. customFrom the resulting mixture cystapep 1 (or its analogues) was isolated

Quellen und Nachweise

ORD-Eintrag
ord-edc3d33e566445458e062f355ce91017
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691805B2

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