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

HRID 1397970Notes

Reaction equation

HRID 1397970 reaction equation
C(N(CC)CC)C.[CH:8]1[C:13](N=C=S)=[CH:12][C:11]2[C:17]([O:19][C:20]3([C:30]4[CH:31]=[CH:32][C:33]([OH:35])=[CH:34][C:29]=4[O:28][C:22]4[CH:23]=[C:24]([OH:27])[CH:25]=[CH:26][C:21]3=4)[C:10]=2[CH:9]=1)=[O:18]>CN(C=O)C>[CH:8]1[CH:13]=[CH:12][C:11]([C:17]([OH:19])=[O:18])=[C:10]([C:20]2[C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:22]=3[O:28][C:29]3[C:30]=2[CH:31]=[CH:32][C:33]([CH:34]=3)=[O:35])[CH:9]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 18730Fluorescein 5-isothiocyanate

Product 1

HCID 33832-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acidYield 81.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under argon atmosphere, to a solution of the crude 21 obtain as above in DMF (3 mL) were successively added triethylamine (29.0 μL, 208 μmol) and fluorescein isothiocyanate isomer I (FITC, 17, commercial product) (90%, HPLC) (45.0 mg, 104 μmol) at room temperature. After stirring for 17 hours at the same temperature, the reaction solution was concentrated under reduced pressure. The residue was purified by flash column chromatography (silica-gel 8 g, dichloromethane/methanol=12/1) to give 1-[2-{(11,12-didehydro-5,6-dihydrodibenzo[a,e]cycloocten-5-yl)oxycarbonylamino}ethyl]-3-(5-fluoresceinyl)thiourea (22) (59.0 mg, 84.8 μmol, 80.7% based on 17) as a yellow solid.

Workup

  1. customat room temperature
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. customThe residue was purified by flash column chromatography (silica-gel 8 g, dichloromethane/methanol=12/1)

Sources & evidence

ORD record
ord-358ae8a2911e4a2eaa21e50ee8e8ba69
Source dataset
uspto-grants-2014_12
Patent number
US08901312B2

Reaction notes

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