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Trifluoroacetic acid → Methyl 2-(3-(dimethylcarbamoyl)-4-nitrophenyl)acetate

HRID 494390
Notes
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Reaction equation

HRID 494390 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH:4]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[C:14]([C:21](=[O:25])[N:22]([CH3:24])[CH3:23])[CH:13]=1)C(OC(C)(C)C)=O.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3](=[O:26])[CH2:4][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[C:14]([C:21](=[O:25])[N:22]([CH3:24])[CH3:23])[CH:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 687608552-(3-Dimethylcarbamoyl-4-nitrophenyl)malonic acid tert-butyl ester methyl ester

Product 1

HCID 57683227Methyl 2-(3-(dimethylcarbamoyl)-4-nitrophenyl)acetateYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The 2-(3-dimethylcarbamoyl-4-nitrophenyl)malonic acid tert-butyl ester methyl ester (1.22 g) obtained in Example 2b) was dissolved in dichloromethane (10 mL), and the solution was cooled to 0° C. After addition of trifluoroacetic acid (10 mL), the mixture was stirred at room temperature for 6 hours, and concentrated, followed by azeotropic distillation with toluene. The residue was purified by column chromatography on silica gel with ethyl acetate:hexane=3:1 to give the title compound (712 mg).

Workup

  1. concentrationconcentrated
  2. distillationfollowed by azeotropic distillation with toluene
  3. customThe residue was purified by column chromatography on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-82bd61dfd8e344c5b49681ce50dda503
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07538140B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes