Trifluoroacetic acid → 3-(3-Pyridyl)alanine [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide

HRID 2120883Notes

Reaction equation

HRID 2120883 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([NH:20][C:21](=[O:38])[C@H:22]([CH2:31][C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)[NH:23]C(OC(C)(C)C)=O)[CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[C:14]1([CH2:13][CH2:12][CH2:11][CH:10]([NH:20][C:21](=[O:38])[C@H:22]([CH2:31][C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)[NH2:23])[CH2:9][CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59885582N-tert-Butoxycarbonyl-3-(3-pyridyl)alanine [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide

Product 1

HCID 129924683-(3-Pyridyl)alanine [4-phenyl-1-(3-phenyl-propyl)-butyl]-amideYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-tert-Butoxycarbonyl-3-(3-pyridyl)alanine [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide (32) (2.08 g; 4.03 mmol) is dissolved in methylene chloride (40 mL) at ambient temperature. Trifluoroacetic acid (20 mL) is added in a slow stream, and the solution is stirred for 4 hours at ambient temperature. The solution is concentrated in vacuo at 40° C. The residue is dissolved in methylene chloride (200 mL) and poured onto saturated sodium bicarbonate solution. The pH is adjusted to 9 with saturated potassium carbonate solution. The mixture is shaken and the layers separated. The water layer is extracted with methylene chloride (3×50 mL). The combined organic extracts are washed with water, dried over MgSO4, filtered, and concentrated in vacuo affording the desired product (1.65 g) as an oil. ESMS: MH− 416.2

Workup

  1. concentrationThe solution is concentrated in vacuo at 40° C
  2. dissolutionThe residue is dissolved in methylene chloride (200 mL)
  3. additionpoured onto saturated sodium bicarbonate solution
  4. stirringThe mixture is shaken
  5. customthe layers separated
  6. extractionThe water layer is extracted with methylene chloride (3×50 mL)
  7. washThe combined organic extracts are washed with water
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ceefa0c7d82540458e68bed052cfaa45
Source dataset
uspto-grants-2004_02
Patent number
US06693099B2

Reaction notes

Loading…