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Trifluoroacetic acid → 5-(N-glycylamino)-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indole

HRID 1637269
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1637269
C(OC([NH:8][CH2:9][C:10]([NH:12][CH:13]1[C:23]2[C:24]3[C:16](=[C:17]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[NH:18][C:19]=3[CH:20]=[CH:21][CH:22]=2)[CH2:15][CH2:14]1)=[O:11])=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[NH2:8][CH2:9][C:10]([NH:12][CH:13]1[C:23]2[C:24]3[C:16](=[C:17]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[NH:18][C:19]=3[CH:20]=[CH:21][CH:22]=2)[CH2:15][CH2:14]1)=[O:11]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 193482985-[N-(N-t-butoxycarbonylglycyl)amino]-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indole

Produkt 1

HCID 193483575-(N-glycylamino)-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indoleAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

A portion (470 mg) of the crude compound obtained in Example 126 was suspended in methylene chloride (4 ml) and to the suspension was added trifluoroacetic acid (4 ml). The mixture was stirred for 1 hour at room temperature. The reaction mixture was made basic with saturated aqueous solution of sodium hydrogencarbonate and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-ethyl acetate/methanol=9:1) to yield 100 mg (41%) of the titled compound.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThen, the solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate-ethyl acetate/methanol=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-3cf1cf431d5b482eb804bdc75085585f
Quelldatensatz
uspto-grants-2000_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06040331

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