Fluorescein 5-isothiocyanate → HCID 178513895, compound

HRID 1666946Notes

Reaction equation

HRID 1666946 reaction equation
[C:1]([O-:32])(=O)[CH2:2][CH2:3][C@H:4]([NH:8][C:9]([C:11]1[CH:30]=[CH:29][C:14]([NH:15][CH2:16][C:17]2[N:28]=[C:27]3[C:20]([N:21]=[C:22]([NH:24][C:25]3=[O:26])[NH2:23])=[N:19][CH:18]=2)=[CH:13][CH:12]=1)=[O:10])[C:5]([OH:7])=[O:6].[CH:33]1[C:38]([N:39]=[C:40]=[S:41])=[CH:37][C:36]2[C:42]([O:44][C:45]3([C:55]4[CH:56]=[CH:57][C:58]([OH:60])=[CH:59][C:54]=4[O:53][C:47]4[CH:48]=[C:49]([OH:52])[CH:50]=[CH:51][C:46]3=4)[C:35]=2[CH:34]=1)=[O:43].[CH3:61][CH2:62][N:63](C(C)C)C(C)C.C[N:71](C)C(N(C)C)=N>CS(C)=O>[CH:30]1[C:11]([C:9]([N:8]([C@H:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2][C:1]([NH2:71])=[O:32])[CH2:61][CH2:62][NH:63][C:40]([NH:39][C:38]2[CH:33]=[CH:34][C:35]3[C:45]4([O:44][C:42](=[O:43])[C:36]=3[CH:37]=2)[C:46]2[CH:51]=[CH:50][C:49]([OH:52])=[CH:48][C:47]=2[O:53][C:54]2[CH:59]=[C:58]([OH:60])[CH:57]=[CH:56][C:55]4=2)=[S:41])=[O:10])=[CH:12][CH:13]=[C:14]([NH:15][CH2:16][C:17]2[N:28]=[C:27]3[C:25]([N:24]=[C:22]([NH2:23])[NH:21][C:20]3=[N:19][CH:18]=2)=[O:26])[CH:29]=1

Participants

6

Reactant 4

HCID 18730Fluorescein 5-isothiocyanateHCID 664601,1,3,3-TetramethylguanidineHCID 81531DiisopropylethylamineHCID 135961629HCID 135961629, compound

Product 1

HCID 178513895HCID 178513895, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

EDA-folate analog 6a was condensed with fluorescein isothiocyanate (FITC, 7) in the presence of DIPEA and 1,1,3,3-tetramethylguanidine (TMG) in DMSO, giving 8a (218 g), which was collected as a precipitate from 1:1 ACN/MTBE. Folate-FITC 8a was purified by reverse phase column chromatography (Biotage C18 cartridge, 100 mM sodium phosphate buffer/acetonitrile as mobile phase). Fractions containing 8a were detected by UV absorption (280 nm) and pooled. Volatile solvents were evaporated, and the residue was desalted by reverse phase column chromatography (Biotage C18 cartridge, water/acetonitrile as mobile phase). Volatile solvents were evaporated, and the residue was lyophilized to give 47 g (22% overall) of 8a. HPLC (Nova-Pak C18 column, 10 mM ammonium acetate/acetonitrile as mobile phase) indicated that the material was greater than 98% pure, and bisfluorescein derivative IIIa (n=1) was not detectable by UV or fluorescence.

Sources & evidence

ORD record
ord-06a3fb2640dd42b9ab6ec2fc8b614055
Source dataset
uspto-grants-2011_10
Patent number
US08044200B2

Reaction notes

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