N-(3-{[(7-{[(3-Hydroxyphenyl)amino]sulfonyl}-9-oxo-9H-fluoren-2-yl)sulfonyl]amino}phenyl)acetamide → N-(3-Aminophenyl)-N'-(3-hydroxyphenyl)-9-oxo-9H-fluorene-2,7-disulfonamide

HRID 2120918Notes

Reaction equation

HRID 2120918 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][S:9]([C:12]2[CH:24]=[C:23]3[C:15]([C:16]4[CH:17]=[CH:18][C:19]([S:26]([NH:29][C:30]5[CH:31]=[C:32]([NH:36]C(=O)C)[CH:33]=[CH:34][CH:35]=5)(=[O:28])=[O:27])=[CH:20][C:21]=4[C:22]3=[O:25])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1>C1COCC1.CO.[OH-].[Na+]>[NH2:36][C:32]1[CH:31]=[C:30]([NH:29][S:26]([C:19]2[CH:18]=[CH:17][C:16]3[C:15]4[C:23](=[CH:24][C:12]([S:9]([NH:8][C:4]5[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=5)(=[O:10])=[O:11])=[CH:13][CH:14]=4)[C:22](=[O:25])[C:21]=3[CH:20]=2)(=[O:27])=[O:28])[CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 1

HCID 9985345N-(3-{[(7-{[(3-Hydroxyphenyl)amino]sulfonyl}-9-oxo-9H-fluoren-2-yl)sulfonyl]amino}phenyl)acetamide

Product 1

HCID 10436736N-(3-Aminophenyl)-N'-(3-hydroxyphenyl)-9-oxo-9H-fluorene-2,7-disulfonamideYield 59.5%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The product from Example 6A (289 mg, 0.554 mmol) in THF:MeOH (1:1, 20 mL) and 15% aq NaOH (10 mL) was heated at reflux. After 24 hours, the volatiles were evaporated at reduced pressure and the residue was partitioned between ethyl acetate and saturated NaHCO3. The separated aqueous phase was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (80% ethyl acetate/hexanes) to provide the title compound as an orange solid (172 mg, 55% yield). 1H NMR (300 MHz, DMSO-d6) δ 9.50 (1H), 7.97-8.1 (m, 4H), 7.92 (d, 2H), 7.00 (t, 1H), 6.83 (t, 1H), 6.58 (t, 1H), 6.53 (m, 1H), 6.42 (m, 1H), 6.35 (t, 1H), 6.22 (m, 2H), 5.14 (bs, 2H). MS (ESI) 520 (M−H)−.

Workup

  1. temperatureat reflux
  2. customthe volatiles were evaporated at reduced pressure
  3. customthe residue was partitioned between ethyl acetate and saturated NaHCO3
  4. extractionThe separated aqueous phase was extracted with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (80% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-fefa999b714d4340b3ef7fda282ec6de
Source dataset
uspto-grants-2004_02
Patent number
US06693136B1

Reaction notes

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