Trifluoroacetic acid → 3-(Piperazin-1-yl)-3-oxopropionic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide

HRID 968707Notes

Reaction equation

HRID 968707 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([NH:20][C:21](=[O:38])[CH2:22][C:23]([N:25]2[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]2)=[O:24])[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:1]1([CH2:7][CH2:8][CH2:9][CH:10]([NH:20][C:21](=[O:38])[CH2:22][C:23]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[O:24])[CH2:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 206224113-[4-(tert-Butoxycarbonyl)piperazin-1-yl]-3-oxopropionic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide

Product 1

HCID 129924703-(Piperazin-1-yl)-3-oxopropionic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[4-(tert-Butoxycarbonyl)piperazin-1-yl]-3-oxopropionic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide (37) (2.05 g; 3.93 mmol) is dissolved in methylene chloride (30 mL) at ambient temperature. Trifluoroacetic acid (15 mL) is added in a slow stream, and the solution is stirred for 1 hour 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 as an oil. ESMS: MH+ 422.2

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-2bc315bc3d764702b4cb6005be020e50
Source dataset
uspto-grants-2007_12
Patent number
US07304053B2

Reaction notes

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