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Benzyloxycarbonylglycine → HCID 131736174, Verbindung

HRID 1052505
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1052505
CCN(C(C)C)C(C)C.[NH2:10][N:11]1[CH:15]=[CH:14][C:13]([Br:16])=[C:12]1[C:17]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:18].[CH2:26]([O:33][C:34]([NH:36][CH2:37][C:38](O)=[O:39])=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>C(OCC)(=O)C>[Br:16][C:13]1[CH:14]=[CH:15][N:11]([NH:10][C:38](=[O:39])[CH2:37][NH:36][C:34](=[O:35])[O:33][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:12]=1[C:17](=[O:18])[NH:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 14349Benzyloxycarbonylglycine2×HCID 81531Diisopropylethylamine2×HCID 111923Propylphosphonic anhydride2×HCID 70979311HCID 70979311, Verbindung

Produkt 1

HCID 131736174HCID 131736174, VerbindungAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel4×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

DIEA (10.5 ml, 60 mmol) was added at 0° C. over a mixture of 1-amino-3-bromo-N-phenyl-1H-pyrrole-2-carboxamide (5.1 g, 18 mmol) and 2-(benzyloxycabonylamino)acetic acid (5.33 g, 25 mmol) in anhydrous ethyl acetate (100 ml). After 15 min T3P® solution (50% AcOEt, 15 ml) was slowly added and stirred 20 min at 0° C. and then at room temperature overnight. Further DIEA (5 ml, 30 mmol), 2-(benzyloxycabonylamino)acetic acid (2.66 g, 25 mmol) and T3P® solution (50% AcOEt, 7 ml) were added and the reaction mixture was stirred at room temperature overnight. More ethyl acetate was added and the reaction crude was washed with water and brine, dried over magnesium sulphate and the solvent was removed under vacuum. The residue was purified by flash chromatography using Isolera® Purification System (0-40%, hexane-AcOEt) to give 7.81 g (41% yield) of the final product with a purity of 45% that was used in the next step without further purification.

Aufarbeitung

  1. customat room temperature
  2. customovernight
  3. stirringthe reaction mixture was stirred at room temperature overnight
  4. customthe reaction crude
  5. washwas washed with water and brine
  6. dry with materialdried over magnesium sulphate
  7. customthe solvent was removed under vacuum
  8. customThe residue was purified by flash chromatography
  9. customIsolera® Purification System (0-40%, hexane-AcOEt)

Quellen und Nachweise

ORD-Eintrag
ord-29a4e3914499492096d83fc6ec8fa133
Quelldatensatz
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09388189B2

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