Dicyclohexylcarbodiimide → 6-Carboxyfluorescein

HRID 973902Notes

Reaction equation

HRID 973902 reaction equation
ON1C(=O)CCC1=O.[CH:9]1[C:14]([C:15]([OH:17])=[O:16])=[CH:13][C:12]2[C:18]3([O:34][C:35](=[O:36])[C:11]=2[CH:10]=1)[C:28]1[CH:29]=[CH:30][C:31]([OH:33])=[CH:32][C:27]=1[O:26][C:20]1[CH:21]=[C:22]([OH:25])[CH:23]=[CH:24][C:19]3=1.C1(N=C=NC2CCCCC2)CCCCC1.[CH2:52]([CH:54]([CH2:58][CH2:59][CH2:60][NH2:61])[C:55]([OH:57])=[O:56])[CH3:53]>N1C=CC=CC=1>[CH:9]1[C:14]([C:15]([OH:17])=[O:16])=[CH:13][C:12]2[C:18]3([O:34][C:35](=[O:36])[C:11]=2[CH:10]=1)[C:28]1[CH:29]=[CH:30][C:31]([OH:33])=[CH:32][C:27]=1[O:26][C:20]1[CH:21]=[C:22]([OH:25])[CH:23]=[CH:24][C:19]3=1.[CH2:52]([CH:54]([CH2:58][CH2:59][CH2:60][NH2:61])[C:55]([OH:57])=[O:56])[CH3:53].[CH:9]1[C:14]([C:15]([OH:17])=[O:16])=[CH:13][C:12]2[C:18]3([O:34][C:35](=[O:36])[C:11]=2[CH:10]=1)[C:28]1[CH:29]=[CH:30][C:31]([OH:33])=[CH:32][C:27]=1[O:26][C:20]1[CH:21]=[C:22]([OH:25])[CH:23]=[CH:24][C:19]3=1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 768066-CarboxyfluoresceinHCID 80170N-HydroxysuccinimideHCID 198801265-Amino-2-ethylpentanoic acid

Product 2

HCID 768066-CarboxyfluoresceinHCID 131715159HCID 131715159, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

An active ester of carboxyfluorescein was prepared by dissolving N-hydroxysuccinimide (5 mg), carboxyfluorescein (7.5 mg) and N,N'-dicyclohexylcarbodiimide (20 mg) in 0.5 ml of pyridine. The reaction was allowed to proceed for two hours at room temperature, after which time 2-ethyl-5-aminopentanoic acid (20 mg) was dissolved in the reaction mixture. The resulting mixture was allowed to react overnight in the dark at room temperature and the reaction product was purified twice employing silica gel thin-layer chromatography using a chloroform:methanol (3:1) mixture as developing solvent to yield a 2-ethyl-5-aminopentanoic acid-carboxyfluorescein conjugate of the formula: ##STR12##

Workup

  1. customto react overnight in the dark at room temperature
  2. customthe reaction product was purified twice employing silica gel thin-layer chromatography

Sources & evidence

ORD record
ord-caec3513a1394141b0fc7bd0d898dbeb
Source dataset
uspto-grants-1991_11
Patent number
US05066426

Reaction notes

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