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

HRID 2387326
Notes
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Reaction equation

HRID 2387326 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents

1
HCID 516892Sodium BicarbonateSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-3a83cc503571493b952797be4abde904
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08268859B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes