Dicyclohexylcarbodiimide → HCID 11840927, compound

HRID 1369319Notes

Reaction equation

HRID 1369319 reaction equation
[OH:1][C:2]([CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1)=O.NCCCCCCO.C1(N=C=NC2CCCCC2)CCCCC1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C([O-])(=O)C.[K+]>CN(C=O)C.C(Cl)Cl>[CH:2](=[O:1])[CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1

Participants

8

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 199606-Amino-1-hexanolHCID 171548BiotinHCID 517044Potassium AcetateHCID 178418287HCID 178418287, compound

Product 1

HCID 11840927HCID 11840927, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Biotin is conjugated to 6-aminohexanol using dicyclohexyl carbodiimide reagent in DMF solvent. The resulting alcohol is oxidized to the aldehyde using pyridinium chlorochromate, potassium acetate in methylene chloride at room temperature (according to the procedure of Ducray et al., J. Org. Chem., 1999, 64:3800-3801). The aldehyde compound is purified by silica column chromatography.

Workup

  1. customat room temperature
  2. customThe aldehyde compound is purified by silica column chromatography

Sources & evidence

ORD record
ord-c8113bfed0ad469891c694353bb5214a
Source dataset
uspto-grants-2003_06
Patent number
US06576752B1

Reaction notes

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