HCID 86684853, compound → 2-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid

HRID 2369474Notes

Reaction equation

HRID 2369474 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([C:23]([OH:25])=[O:24])=[C:5]([C:7]2[C:17]3[CH:18]=[CH:19][C:20]([OH:22])=[CH:21][C:16]=3[O:15][C:14]3[C:8]=2[CH:9]=[CH:10][C:11]([CH:13]=3)=[O:12])[CH:6]=1.[N-]=[N+]=[N-]>O1CCCC1.CS(C)=O>[CH:1]1[CH:2]=[CH:3][C:4]([C:23]([OH:25])=[O:24])=[C:5]([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([OH:12])=[CH:13][C:14]=3[O:15][C:16]3[C:17]=2[CH:18]=[CH:19][C:20]([CH:21]=3)=[O:22])[CH:6]=1

Participants

4

Reactant 1

HCID 86684853HCID 86684853, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 500 μL of a 0.2 mM solution of [DBCO-Lys(mPEG5kD)]8[Lys]4[Lys]2Lys-DAB-DNP in tetrahydrofuran was added 103 μL of the 11.7 mM linked fluorescein azide solution in DMSO prepared in Example 34. The reaction solution was incubated in the dark for 17 hours at which time HPLC analysis indicated complete consumption of the fluorescein azide. A further 50 μL aliquot of the linked fluorescein azide was added and the reaction incubated in the dark for 24 hours. HPLC analysis now showed residual fluorescein azide. The reaction solution was diluted with water (2 mL) and was dialysed (MWCO 12-14K) against 10 mM sodium acetate, pH 5, (250 mL) for 22 hours in the dark. The buffer was replaced with methanol (250 mL) and the dialysis continued for 7 hours with a change of solvent after 4 hours. The retentate was concentrated on the roto-vap. Compounds include those wherein R1 is phenylsulfonyl, 4-chlorophenylsulfonyl and morpholinosulfonyl.

Workup

  1. customconsumption of the fluorescein azide
  2. additionA further 50 μL aliquot of the linked fluorescein azide was added
  3. waitthe reaction incubated in the dark for 24 hours
  4. additionThe reaction solution was diluted with water (2 mL)
  5. customwas dialysed (MWCO 12-14K) against 10 mM sodium acetate, pH 5, (250 mL) for 22 hours in the dark
  6. customthe dialysis
  7. waitcontinued for 7 hours with a change of solvent after 4 hours
  8. concentrationThe retentate was concentrated on the roto-vap

Sources & evidence

ORD record
ord-d89d7b7fde2747cfa89b874157c8fa51
Source dataset
uspto-grants-2014_04
Patent number
US08703907B2

Reaction notes

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