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Water → HCID 70047752, Verbindung

HRID 1080921
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1080921
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[CH2:22]([O:29][C:30]([NH:32][C@H:33]([C:37]([NH:39][C@@H:40]([CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[C@H:41]([OH:56])[CH2:42][C@@H:43]1[CH2:48][CH2:47][CH2:46][CH2:45][C@H:44]1[C:49]([NH:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])=[O:38])[CH:34]([CH3:36])[CH3:35])=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>CN(C)C=O>[CH2:22]([O:29][C:30]([NH:32][C@H:33]([C:37]([NH:39][C@@H:40]([CH2:57][C:58]1[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=1)[C:41](=[O:56])[CH2:42][C@@H:43]1[CH2:48][CH2:47][CH2:46][CH2:45][C@H:44]1[C:49]([NH:51][C:52]([CH3:54])([CH3:55])[CH3:53])=[O:50])=[O:38])[CH:34]([CH3:36])[CH3:35])=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 962WaterHCID 2724130Cornforth reagentHCID 70049680HCID 70049680, Verbindung

Produkt 1

HCID 70047752HCID 70047752, VerbindungAusbeute 67,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

220 mg (0.59 mmol) of pyridinium dichromate were added to a solution of 48 mg (0.08 mmol) of 2(S)-[3(S)-[[N-(benzyloxycarbonyl)-L-valyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-1(R)-cyclohexanecarboxamide in 1 ml of dimethylformamide and the mixture was stirred at room temperature for 18 hours. 10 ml of water were added and the mixture was extracted with two 10 ml portions of ethyl acetate. The combined extracts were washed with two 10 ml portions of water, dried over anhydrous magnesium sulphate and evaporated; The crude product was chromatographed on a column of silica gel using 4% methanol in dichloromethane for the elution to give 31 mg of 2(S)-[3(S)-[[N-(benzyloxycarbonyl)-L-valyl]amino]-2-oxo-4-phenylbutyl]-N-tert.butyl-1(R)-cyclohexanecarboxamide as a white solid of melting point 186°-188° C.; MS m/e 578 [M+H]+.

Aufarbeitung

  1. extractionthe mixture was extracted with two 10 ml portions of ethyl acetate
  2. washThe combined extracts were washed with two 10 ml portions of water
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customevaporated
  5. customThe crude product was chromatographed on a column of silica gel using 4% methanol in dichloromethane for the elution

Quellen und Nachweise

ORD-Eintrag
ord-fa76277aa0db4e278f1cc32c0fc7d589
Quelldatensatz
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05583248

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