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

HRID 617683Notes

Reaction equation

HRID 617683 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5565c67d56f746eb8a2c86c07a4205b6
Source dataset
uspto-grants-1999_09
Patent number
US05952185

Reaction notes

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