Potassium Carbonate → HCID 64700590, compound

HRID 1485479Notes

Reaction equation

HRID 1485479 reaction equation
[NH2:1][C:2]([CH3:8])([CH3:7])[CH2:3][C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].F[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23]>CCO>[CH3:7][C:2]([NH:1][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23])([CH3:8])[CH2:3][C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 27609333-Amino-3-methylbutanoic acid

Product 1

HCID 64700590HCID 64700590, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A round bottomed flask was charged with 3-amino-3-methylbutanoic acid (1.452 g, 12.39 mmol), potassium carbonate (2.57 g, 18.59 mmol), and a stirbar. EtOH (20 mL, 0.5 M) was added, followed by 1-fluoro-2-nitrobenzene (2.84 ml, 15.49 mmol), and the solution was stirred at reflux overnight. The mixture was cooled, concentrated with celite, and purified by silica gel chromatography (eluting with methylene chloride/methanol/ammonium hydroxide) to yield 3-methyl-3-(2-nitrophenylamino)butanoic acid as a red solid (2.32 g, 9.73 mmol, 79%).

Workup

  1. temperatureat reflux overnight
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated with celite
  4. custompurified by silica gel chromatography (eluting with methylene chloride/methanol/ammonium hydroxide)

Sources & evidence

ORD record
ord-2137317599ba4d7d94bfa4457daa0df2
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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