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

HRID 720920Notes

Reaction equation

HRID 720920 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 94.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-tert-Butoxycarbonyl-3-(3-pyridyl)-alanine [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide (84) (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 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 (1.59 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 the layers
  5. customseparated
  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-2e5a9aaf308745e0ac0c60af91ca6aaa
Source dataset
uspto-grants-2006_11
Patent number
US07135483B2

Reaction notes

Loading…