6-Carboxyfluorescein → 2-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid

HRID 1034600Notes

Reaction equation

HRID 1034600 reaction equation
[CH:1]1[C:6](C(O)=O)=[CH:5][C:4]2[C:10]3([O:26][C:27](=[O:28])[C:3]=2[CH:2]=1)[C:19]1[CH:20]=[CH:21][C:22]([OH:24])=[CH:23][C:18]=1[O:17][C:16]1[CH:15]=[C:14]([OH:25])[CH:13]=[CH:12][C:11]3=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[CH:6]1[CH:1]=[CH:2][C:3]([C:27]([OH:28])=[O:26])=[C:4]([C:10]2[C:11]3[CH:12]=[CH:13][C:14]([OH:25])=[CH:15][C:16]=3[O:17][C:18]3[C:19]=2[CH:20]=[CH:21][C:22]([CH:23]=3)=[O:24])[CH:5]=1

Participants

5

Reactant 3

HCID 768066-CarboxyfluoresceinHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 33832-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

5(6)-carboxy fluorescein is dissolved in NMP to a concentration of 0.2 M. Activation is performed with 0.9 eq. HATU and 1 eq. DIPEA for 2 min before coupling for at least 2×20 min or until the Kaiser test is negative.

Sources & evidence

ORD record
ord-c0da6965385c4e94892ebde574e24b51
Source dataset
uspto-grants-2013_10
Patent number
US08546309B2

Reaction notes

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