Trifluoroacetic acid → (2R)-N-Methyl-2-(methylamino)-3-phenyl-N-(2-(2-pyridyl)ethyl)propionamide

HRID 413490Notes

Reaction equation

HRID 413490 reaction equation
C(O[C:6](=O)[N:7](C)[C@@H:8]([C:16](=[O:27])[N:17]([CH3:26])[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)[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>ClCCl>[CH3:26][N:17]([CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)[C:16](=[O:27])[C@H:8]([NH:7][CH3:6])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59063568n-Methyl-n{(1r)-1-[n-methyl-n-(2-(2-pyridyl)ethyl)carbamoyl]-2-phenylethyl}carbamic acid tert-butyl ester

Product 1

HCID 53710542(2R)-N-Methyl-2-(methylamino)-3-phenyl-N-(2-(2-pyridyl)ethyl)propionamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Methyl-N{(1R)-1-[N-methyl-N-(2-(2-pyridyl)ethyl)carbamoyl]-2-phenylethyl}carbamic acid tert-butyl ester was dissolved in dichloromethane (75 mL). Trifluoroacetic acid (75 mL, 0.978 mol) was added to the stirred solution. The reaction mixture was stirred for 40 min. The solvent was removed in vacuo. The product was dissolved in dichloromethane (30 mL) and sat. aqueous sodium hydrogen carbonate solution (20 mL). The reaction mixture was neutralised with solid sodium hydrogen carbonate. Dichloromethane (100 mL) was added and the aqueous phase was extracted with dichloromethane (2×150 mL). The combined organic layers were dried over magnesium sulfate. The solvent was removed in vacuo, to give 7.9 g of (2R)-N-Methyl-2-(methylamino)-3-phenyl-N-(2-(2-pyridyl)ethyl)propionamide.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe product was dissolved in dichloromethane (30 mL)
  3. additionDichloromethane (100 mL) was added
  4. extractionthe aqueous phase was extracted with dichloromethane (2×150 mL)
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-aff46a5246ab462f9a0cd982dead3acc
Source dataset
uspto-grants-2003_05
Patent number
US06566337B1

Reaction notes

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