Trifluoroacetic acid → 4-Benzyloxy-1-[2-(4-methylaminomethyl-phenyl)-ethyl]-1H-pyridin-2-one

HRID 564162Notes

Reaction equation

HRID 564162 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][N:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:20][C:19]2=[O:32])=[CH:12][CH:11]=1)C)(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[CH2:25]([O:24][C:21]1[CH:22]=[CH:23][N:18]([CH2:17][CH2:16][C:13]2[CH:14]=[CH:15][C:10]([CH2:9][NH:7][CH3:6])=[CH:11][CH:12]=2)[C:19](=[O:32])[CH:20]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67006987{4-[2-(4-Benzyloxy-2-oxo-2H-pyridin-1-yl)-ethyl]-benzyl}-methyl-carbamic Acid Tert-Butyl Ester

Product 1

HCID 580428054-Benzyloxy-1-[2-(4-methylaminomethyl-phenyl)-ethyl]-1H-pyridin-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To 100 mg (0.22 mmol) {4-[2-(4-benzyloxy-2-oxo-2H-pyridin-1-yl)-ethyl]-benzyl}-methyl-carbamic acid tert-butyl ester (example 19.1a) in DCM is added at RT 0.70 mL trifluoro-acetic acid. The reaction mixture is stirred 2 h at RT, neutralized with aqueous saturated NaHCO3-solution and is diluted with water and DCM. The layers are separated, the aqueous phase is extracted twice with DCM. The combined organic phase is dried over MgSO4, filtered and the solvent is evaporated. The residue is purified via reverse HPLC chromatography (Waters symmetry, C18; water (0.1% formic acid)/acetonitrile (0.1% formic acid) 95:5 to 10:90).

Workup

  1. customThe layers are separated
  2. extractionthe aqueous phase is extracted twice with DCM
  3. dry with materialThe combined organic phase is dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent is evaporated
  6. customThe residue is purified via reverse HPLC chromatography (Waters symmetry, C18; water (0.1% formic acid)/acetonitrile (0.1% formic acid) 95:5 to 10:90)

Sources & evidence

ORD record
ord-fe6e93aa3a3344ee81f01348629ece05
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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