Trifluoroacetic acid → (2-Cyanophenyl)alanine dihexylamide

HRID 651583Notes

Reaction equation

HRID 651583 reaction equation
[CH2:1]([N:7]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[C:8](=[O:27])[C@H:9]([CH3:26])[N:10]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]#[N:25])C(OC(C)(C)C)=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].FC(F)(F)C(O)=O>ClCCl>[CH2:28]([N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:8](=[O:27])[C@H:9]([CH3:26])[NH:10][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]#[N:25])[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53745284HCID 53745284, compound

Product 1

HCID 54368029(2-Cyanophenyl)alanine dihexylamideYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.98 g of N-t-butoxycarbonyl-(2-cyanophenyl)alanine dihexylamide in 1.7 ml of dichloromethane was added 1.7 ml of trifluoroacetic acid, followed by stirring at room temperature for 1.5 hours. The reaction solution was concentrated under reduced pressure, and to the residue was added an aqueous sodium bicarbonate solution, followed by extracting with dichloromethane. The extract was washed with a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure to give 0.76 g of a crude (2-cyanophenyl)alanine dihexylamide, which was then used for the next step without purification.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionto the residue was added an aqueous sodium bicarbonate solution
  3. extractionby extracting with dichloromethane
  4. washThe extract was washed with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter removal of the drying agent
  7. filtrationby filtration
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6adeffc1edd14588bb24cee98e66863c
Source dataset
uspto-grants-2001_08
Patent number
US06281355B1

Reaction notes

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