Trifluoroacetic acid → (S)-2-amino-N,N-dimethyl-3-phenylpropanamide

HRID 1879465Notes

Reaction equation

HRID 1879465 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:16](=[O:20])[N:17]([CH3:19])[CH3:18])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:7][C@@H:8]([CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:16]([N:17]([CH3:19])[CH3:18])=[O:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 14541824tert-Butyl (S)-(1-(dimethylamino)-1-oxo-3-phenylpropan-2-yl)carbamate

Product 1

HCID 11008771(S)-2-amino-N,N-dimethyl-3-phenylpropanamideYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

((S)-1-Dimethylcarbamoyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester (2.0 g, 6.85 mmol) was dissolved in methylene chloride (20 mL) at 0° C. Trifluoroacetic acid (20 mL) was added. The mixture was stirred for 2 h and evaporated. The residue was dissolved in methylene chloride and very carefully basified using saturated aqueous sodium bicarbonate. The organic layer was separated and the aqueous layer was extracted using methylene chloride. The combined organic extracts were washed with water and brine, and then dried over sodium sulfate to give (S)-2-amino-N,N-dimethyl-3-phenyl-propionamide (1.0 g, 76%) as yellow oil.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in methylene chloride
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted
  5. washThe combined organic extracts were washed with water and brine
  6. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-358dc480b1dc4c308e745e2478c890fb
Source dataset
uspto-grants-2012_11
Patent number
US08314250B2

Reaction notes

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