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[9-Benzyl-4-carbamoyl-7-methoxy-1,2,3,4-tetrahydrocarbazol-5-yl]oxyacetic acid sodium salt → [9-Benzyl-4-carbamoyl-7-methoxycarbazol-5-yl]oxyacetic acid

HRID 51310
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 51310
[Na+].[CH2:2]([N:9]1[C:21]2[CH2:20][CH2:19][CH2:18][CH:17]([C:22](=[O:24])[NH2:23])[C:16]=2[C:15]2[C:10]1=[CH:11][C:12]([O:30][CH3:31])=[CH:13][C:14]=2[O:25][CH2:26][C:27]([O-:29])=[O:28])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>[Pd].CCOCCOCCO>[CH2:2]([N:9]1[C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([C:22](=[O:24])[NH2:23])[C:16]=2[C:15]2[C:10]1=[CH:11][C:12]([O:30][CH3:31])=[CH:13][C:14]=2[O:25][CH2:26][C:27]([OH:29])=[O:28])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 1

HCID 23676539[9-Benzyl-4-carbamoyl-7-methoxy-1,2,3,4-tetrahydrocarbazol-5-yl]oxyacetic acid sodium salt

Produkt 1

HCID 10135839[9-Benzyl-4-carbamoyl-7-methoxycarbazol-5-yl]oxyacetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8146Diethylene Glycol Monoethyl EtherLösungsmittel

Versuchsvorschrift

A mixture of 430 mg. of the product from Example 3 Part D, 2.0 gm. of 5% Pd/C, and 20 mL of carbitol was heated to reflux and refluxed for 21 hours, cooled, and filtered. The filtrate was diluted with water, acidified with hydrochloric acid, and extracted well with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue was triturated with dichloromethane and filtered to remove solid tetrahydrocarbazole. The filtrate was evaporated in vacuo to give the title product, 125 mg, 31%.

Aufarbeitung

  1. additionA mixture of 430 mg
  2. temperatureto reflux
  3. temperaturerefluxed for 21 hours
  4. temperaturecooled
  5. filtrationfiltered
  6. additionThe filtrate was diluted with water
  7. extractionextracted well with ethyl acetate
  8. washThe organic phase was washed with brine
  9. dry with materialdried over sodium sulfate
  10. customevaporated in vacuo
  11. customThe residue was triturated with dichloromethane
  12. filtrationfiltered
  13. customto remove solid tetrahydrocarbazole
  14. customThe filtrate was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1987d5e7313946f0bcb447800840db56
Quelldatensatz
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06713645B1

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