Triethylamine → Biotin [2-(4-azidobenzoyl)aminohexyl]amidE

HRID 617683

Reaktionsgleichung

Reaktionsgleichung von HRID 617683
[N:1]([C:4]1[CH:19]=[CH:18][C:7]([C:8]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]CN)=[O:9])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].[CH2:20]([N:22](CC)CC)C.C1C(=O)N([O:34][C:35]([CH2:37][CH2:38][CH2:39][CH2:40][CH:41]2[S:45][CH2:44][CH:43]3[NH:46][C:47]([NH:49][CH:42]23)=[O:48])=[O:36])C(=O)C1>CN(C=O)C>[OH:36][C:35]([CH2:37][CH2:38][CH2:39][CH2:40][C@H:41]1[C@@H:42]2[C@@H:43]([NH:46][C:47]([NH:49]2)=[O:48])[CH2:44][S:45]1)=[O:34].[N:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][CH:11]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:20][NH-:22])=[O:9])=[CH:18][CH:19]=1)=[N+:2]=[N-:3]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 434213NHS-BiotinHCID 13330101N-(6-Aminohexyl)-4-azidobenzamide

Produkt 1

HCID 131721358Biotin [2-(4-azidobenzoyl)aminohexyl]amidE

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

1.30 g (5 mmol) of product 2b are suspended in 40 ml of distilled DMF and 1.4 ml triethylamine are added under stirring at 20° C. Subsequently, 1.71 g (5 mmol) of biotin-N-hydroxysuccinimide ester 3 are added and stirring is continued for another 3 h at 20° C. Subsequently, the solvent is removed on a rotation evaporator (oil pump vacuum, water bath 50° C.) and the concentrated residue is digested overnight with saturated NaHCO3 solution. Product 4b is drawn off, washed with water and dried in the exsiccator.

Aufarbeitung

  1. stirringstirring
  2. customSubsequently, the solvent is removed on a rotation evaporator (oil pump vacuum, water bath 50° C.)
  3. waitthe concentrated residue is digested overnight with saturated NaHCO3 solution
  4. washwashed with water
  5. customdried in the exsiccator

Quellen und Nachweise

ORD-Eintrag
ord-5565c67d56f746eb8a2c86c07a4205b6
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05952185

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