Dicyclohexylcarbodiimide → 6-Carboxyfluorescein

HRID 1632531Notes

Reaction equation

HRID 1632531 reaction equation
[CH:1]1[C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]([C:10]2[C:20]3[CH:21]=[CH:22][C:23]([OH:25])=[CH:24][C:19]=3[O:18][C:17]3[C:11]=2[CH:12]=[CH:13][C:14]([CH:16]=3)=[O:15])=[C:3]([C:26]([OH:28])=[O:27])[CH:2]=1.[OH:29][N:30]1[C:34](=[O:35])[CH2:33][CH2:32][C:31]1=[O:36].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[OH:29][N:30]1[C:34](=[O:35])[CH2:33][CH2:32][C:31]1=[O:36].[CH:1]1[C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]2[C:10]3([O:27][C:26](=[O:28])[C:3]=2[CH:2]=1)[C:11]1[CH:12]=[CH:13][C:14]([OH:15])=[CH:16][C:17]=1[O:18][C:19]1[CH:24]=[C:23]([OH:25])[CH:22]=[CH:21][C:20]3=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 2725051ST51005980

Product 2

HCID 768066-CarboxyfluoresceinHCID 80170N-Hydroxysuccinimide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To 83 mg (0.22 mmol) of 6-carboxyfluorescein dissolved in 2 ml of dimethylformamide was added 28 mg (0.24 mmol) of N-hydroxysuccinimide and 55 mg (0.27 mmol) of N,N'-dicyclohexylcarbodiimide. The reaction mixture was stirred at 0° C. under argon atmosphere for one hour and then maintained at 4° C. for 16 hours to yield a N-hydroxysuccinimide active ester of carboxyfluorescein having the formula: ##STR5##

Workup

  1. temperaturemaintained at 4° C. for 16 hours

Sources & evidence

ORD record
ord-b65a92f826d64feaa5c77daffbc69a5a
Source dataset
uspto-grants-1984_10
Patent number
US04476228

Reaction notes

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