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Sodium Carbonate → tert-butyl 2-[(2-ethoxymethyl-5-oxido-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl)oxy]ethylcarbamate

HRID 2203492
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2203492
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[C:12]([O:16][C:17](=[O:42])[NH:18][CH2:19][CH2:20][O:21][C:22]1[CH:31]=[CH:30][C:29]2[N:28]=[CH:27][C:26]3[N:32]=[C:33]([CH2:38][O:39][CH2:40][CH3:41])[N:34]([CH2:35][CH2:36][CH3:37])[C:25]=3[C:24]=2[CH:23]=1)([CH3:15])([CH3:14])[CH3:13].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:40]([O:39][CH2:38][C:33]1[N:34]([CH2:35][CH2:36][CH3:37])[C:25]2[C:24]3[CH:23]=[C:22]([O:21][CH2:20][CH2:19][NH:18][C:17](=[O:42])[O:16][C:12]([CH3:13])([CH3:14])[CH3:15])[CH:31]=[CH:30][C:29]=3[N+:28]([O-:9])=[CH:27][C:26]=2[N:32]=1)[CH3:41]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 131731977tert-butyl[2-(2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-8-yloxy)ethyl]carbamate

Produkt 1

HCID 68973926tert-butyl 2-[(2-ethoxymethyl-5-oxido-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl)oxy]ethylcarbamateAusbeute 64,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212
Chloroform
Lösungsmittel
2×

Versuchsvorschrift

mCPBA (60% pure, 12.76 g, 44.36 mmol) was added in one portion to a solution of tert-butyl[2-(2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-8-yloxy)ethyl]carbamate (14.4 g, 33.6 mmol) and chloroform (150 mL); the reaction mixture was stirred for 30 minutes. The reaction mixture was then poured into saturated aqueous sodium carbonate (100 mL) and stirred for 30 minutes. Chloroform (250 mL) was added, and the organic fraction was washed sequentially with 5% aqueous sodium carbonate, water, and brine; dried over magnesium sulfate; filtered; and concentrated under reduced pressure. The resulting red oil was triturated with ethyl acetate to provide 9.7 g of tert-butyl 2-[(2-ethoxymethyl-5-oxido-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl)oxy]ethylcarbamate as a peach-colored powder.

Aufarbeitung

  1. stirringstirred for 30 minutes
  2. washthe organic fraction was washed sequentially with 5% aqueous sodium carbonate, water, and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationand concentrated under reduced pressure
  6. customThe resulting red oil was triturated with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b2f6e5290f9b44c2a0e98929e8b2f5de
Quelldatensatz
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09365567B2

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