Trifluoroacetic acid → (2R)-3-(4-fluorophenyl)-N-methyl-2-methylaminopropionamide

HRID 495794Notes

Reaction equation

HRID 495794 reaction equation
C(O[C:6](=O)[N:7]([C@@H:9]([C:18](=[O:21])[NH:19][CH3:20])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)C)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+].C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl>[F:17][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][C@@H:9]([NH:7][CH3:6])[C:18]([NH:19][CH3:20])=[O:21])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10791Sodium SesquicarbonateHCID 516892Sodium BicarbonateHCID 10828758((1R)-2-(4-fluorophenyl)-1-(methylcarbamoyl)ethyl)-methylcarbamic acid tert-butylester

Product 1

HCID 10560386(2R)-3-(4-fluorophenyl)-N-methyl-2-methylaminopropionamideYield 91.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

((1R)-2-(4-Fluorophenyl)-1-(methylcarbamoyl)ethyl)-methylcarbamic acid tert-butylester (1.0 g; 3.22 mmol) was dissolved in methylene chloride (5 mL). Trifluoroacetic acid (5 mL) was added and the reaction mixture was stirred for 30 min at room temperature. Methylene chloride (30 mL), an aqueous solution of sodium hydrogen carbonate/sodium carbonate (pH 9; 30 mL) and sodium hydrogen carbonate (solid), were added to the reaction mixture, until pH 9. The organic phase was dried (magnesium sulfate) and evaporated in vacuo to afford 0.62 g of (2R)-3-(4-fluorophenyl)-N-methyl-2-methylaminopropionamide.

Workup

  1. dry with materialThe organic phase was dried (magnesium sulfate)
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-4a6ef887c98a4a7db5cc483aea19c211
Source dataset
uspto-grants-2005_09
Patent number
US06939880B2

Reaction notes

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