HCID 12093195, compound → (2,7-bis{[(3-Hydroxyphenyl)amino]sulfonyl}-9H-fluoren-9-ylidene)acetic Acid

HRID 2120915Notes

Reaction equation

HRID 2120915 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][S:9]([C:12]2[CH:24]=[CH:23][C:22]3[C:21]4[C:16](=[CH:17][C:18]([S:25]([NH:28][C:29]5[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=5)(=[O:27])=[O:26])=[CH:19][CH:20]=4)[C:15](=[CH:36][C:37]([O:39]CC)=[O:38])[C:14]=3[CH:13]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1>C1COCC1.[OH-].[Na+]>[OH:1][C:2]1[CH:3]=[C:4]([NH:8][S:9]([C:12]2[CH:24]=[CH:23][C:22]3[C:21]4[C:16](=[CH:17][C:18]([S:25]([NH:28][C:29]5[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=5)(=[O:26])=[O:27])=[CH:19][CH:20]=4)[C:15](=[CH:36][C:37]([OH:39])=[O:38])[C:14]=3[CH:13]=2)(=[O:10])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 12093195HCID 12093195, compound

Product 1

HCID 10053631(2,7-bis{[(3-Hydroxyphenyl)amino]sulfonyl}-9H-fluoren-9-ylidene)acetic AcidYield 22%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

The product from Example 5A (460 mg, 0.78 mmol) in THF (5 mL) and 15% aqueous NaOH (5 mL) was heated at reflux for 6 hours. The mixture was allowed to cool to ambient temperature, acidified, and extracted with ethyl acetate. The organic phase was separated, washed with brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure to provide the title compound as a yellow solid (95 mg, 22% yield). 1H NMR (300 MHz, DMSO-d6) δ 10.26 (s, 1H), 10.16 (s, 1H), 9.43 (s, 1H), 9.18 (d, 1H), 8.37 (d, 1H), 8.1 (m, 2H), 7.86 (m, 2H), 7.2 (s, 1H), 7.0 (t, 2H), 6.53-6.63(m, 4H), 6.42 (m, 2H). MS (ESI) 563 (M−H)−.

Workup

  1. temperatureat reflux for 6 hours
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-4124d2fabaad40c6bc36e3428eece037
Source dataset
uspto-grants-2004_02
Patent number
US06693136B1

Reaction notes

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