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Bromoacetyl bromide → {2-[(2-Bromoacetyl)-(2-chloro-5-fluorophenyl)amino]-1,1-dimethylethyl}carbamic acid t-butyl ester

HRID 1694930
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1694930
[Br:1][CH2:2][C:3](Br)=[O:4].[C:6]([O:10][C:11](=[O:26])[NH:12][C:13]([CH3:25])([CH3:24])[CH2:14][NH:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[Cl:23])([CH3:9])([CH3:8])[CH3:7].C(=O)(O)[O-].[Na+]>CN(C)C(=O)C>[C:6]([O:10][C:11](=[O:26])[NH:12][C:13]([CH3:25])([CH3:24])[CH2:14][N:15]([C:3](=[O:4])[CH2:2][Br:1])[C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[Cl:23])([CH3:9])([CH3:7])[CH3:8]
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Komponenten

5

Edukt 3

HCID 61147Bromoacetyl bromideHCID 516892Sodium BicarbonateHCID 66645618HCID 66645618, Verbindung

Produkt 1

HCID 66645632{2-[(2-Bromoacetyl)-(2-chloro-5-fluorophenyl)amino]-1,1-dimethylethyl}carbamic acid t-butyl esterAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374Dimethylacetamide
Lösungsmittel

Versuchsvorschrift

2.2 ml of bromoacetyl bromide (25.2 mmol) was added to a solution of 5.3 g of [2-(2-chloro-5-fluorophenylamino)-1,1-dimethylethyl]carbamic acid t-butyl ester obtained in Example (62a) (16.8 mmol) in N,N-dimethylacetamide (170 ml) under ice-cooling, and the mixture was stirred at the same temperature for 15 minutes. A saturated sodium bicarbonate aqueous solution was added to the reaction mixture, followed by extraction with ethyl acetate. Then, the organic layer was washed with water and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. Hexane was added to the residue, and the solid was collected by filtration to obtain 5.8 g of the title compound (yield: 80%).

Aufarbeitung

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThen, the organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. additionHexane was added to the residue
  8. filtrationthe solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-748779d423d8449280ac81ec4b33eca7
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08158790B2

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