Sodium Bicarbonate → tert-butyl{[5-bromo-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate

HRID 1012426Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1012426
[Br:1][C:2]1[N:6]([S:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:5]=[C:4]([CH2:16][NH:17][CH3:18])[CH:3]=1.[C:19](=[O:22])([O-])[OH:20].[Na+]>C(OCC)(=O)C>[C:4]([O:20][C:19](=[O:22])[N:17]([CH2:16][C:4]1[CH:3]=[C:2]([Br:1])[N:6]([S:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:5]=1)[CH3:18])([CH3:16])([CH3:5])[CH3:3]

Komponenten

4

Edukt 2

HCID 516892Sodium BicarbonateHCID 669246631-[5-bromo-1-(phenylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine

Produkt 1

HCID 66924909tert-butyl{[5-bromo-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamateAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1-[5-bromo-1-(phenylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine (4.4 g) in ethyl acetate (60 mL) was added di-tert-butyl bicarbonate (2.8 mL), and the mixture was stirred at room temperature for 14 hr. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=4:1) to give the title compound as a colorless oil (yield 3.4 g, 73%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-1f648ccfed624f938da2f57076b78db5
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977488B2

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