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Dimethylformamide → 2-[1,1-dimethyl-2-((R)-2-trifluoromethyloxiranyl)ethyl]benzamide

HRID 2387326
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2387326
C[N:2]([CH:4]=[O:5])C.[CH3:6][C:7]([C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1C(O)=O)([CH3:16])[CH2:8][C@:9]1([C:12]([F:15])([F:14])[F:13])[CH2:11][O:10]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[OH-].[NH4+]>C(=O)(O)[O-].[Na+]>[CH3:16][C:7]([C:17]1[CH:18]=[CH:22][CH:23]=[CH:24][C:25]=1[C:4]([NH2:2])=[O:5])([CH3:6])[CH2:8][C@:9]1([C:12]([F:13])([F:14])[F:15])[CH2:11][O:10]1
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Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 498213602-[1,1-dimethyl-2-((R)-2-trifluoromethyloxiranyl)ethyl]benzoic acid

Produkt 1

HCID 580261682-[1,1-dimethyl-2-((R)-2-trifluoromethyloxiranyl)ethyl]benzamide

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A stirred, ice-cooled, DMF (60 mL) solution of the 2-[1,1-dimethyl-2-((R)-2-trifluoromethyloxiranyl)ethyl]benzoic acid (8.5 g, ˜80%, 23.6 mmol) triethylamine (6.6 mL, 47.2 mmol) was added and after 2-3 minutes TBTU (8.3 g, 26 mmol) was added. After stirring for 30 minutes, ammonium hydroxide solution (7 mL, 98 mmol) was added and stirred for 40 minutes. The reaction mixture was diluted with 500 mL of saturated aqueous sodium bicarbonate solution and extracted with three 200 mL portions of dichloromethane. The combined organic extracts were washed with saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, and the solvent evaporated in vacuo to give 2-[1,1-dimethyl-2-((R)-2-trifluoromethyloxiranyl)ethyl]benzamide as a colorless thick oil which solidified on standing (6.0 g, 90%).

Aufarbeitung

  1. temperatureA stirred, ice-cooled
  2. additionwas added
  3. stirringstirred for 40 minutes
  4. extractionextracted with three 200 mL portions of dichloromethane
  5. washThe combined organic extracts were washed with saturated aqueous sodium bicarbonate solution and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3a83cc503571493b952797be4abde904
Quelldatensatz
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08268859B2

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