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Water → 3-(N-Boc-6-aminocaproyl)amino-9-ethylcarbazole

HRID 50604
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 50604
[C:1]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH2:17][C:18]1[CH:19]=[CH:20][C:21]2[N:22]([CH2:31][CH3:32])[C:23]3[C:28]([C:29]=2[CH:30]=1)=[CH:27][CH:26]=[CH:25][CH:24]=3.CCN=C=NCCCN(C)C.Cl.O>CN(C)C=O>[C:1]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH:17][C:18]1[CH:19]=[CH:20][C:21]2[N:22]([CH2:31][CH3:32])[C:23]3[C:28]([C:29]=2[CH:30]=1)=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:16])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]
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Komponenten

6

Edukt 4

HCID 962WaterHCID 85883-Amino-9-ethylcarbazoleHCID 6376026-((tert-Butoxycarbonyl)amino)hexanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 227361413-(N-Boc-6-aminocaproyl)amino-9-ethylcarbazoleAusbeute 74,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

N-Boc-6-aminocaproic acid (7.58 g) prepared by the method described in a Journal of Medicinal Chemistry (J. Med. Chem., 35, p.272 (1993)) and 7.58 g of 3-amino-9-ethylcarbazole were dissolved in 75 mL of dimethylformamide, and the solution was added with 10.4 g WSC hydrochloride and stirred at room temperature for 3.5 hours. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with 1 N aqueous sodium hydroxide, 10% aqueous citric acid and saturated brine, then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluent: hexane/ethyl acetate=1/1) to obtain 10.3 g of 3-(N-Boc-6-aminocaproyl)amino-9-ethylcarbazole.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with 1 N aqueous sodium hydroxide, 10% aqueous citric acid and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (eluent: hexane/ethyl acetate=1/1)

Quellen und Nachweise

ORD-Eintrag
ord-16b09f52008b4c84bef09708dddba54b
Quelldatensatz
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06713473B1

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