StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

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 2120918
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2120918
[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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 1

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

Produkt 1

HCID 10436736N-(3-Aminophenyl)-N'-(3-hydroxyphenyl)-9-oxo-9H-fluorene-2,7-disulfonamideAusbeute 59,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14798Sodium HydroxideLösungsmittelHCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

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)−.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-fefa999b714d4340b3ef7fda282ec6de
Quelldatensatz
uspto-grants-2004_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06693136B1

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion