Trifluoroacetic acid → 3-({4-[3-(3-Chlorophenyl)-4-(3,4-dimethylphenyl)but-1-yn-1-yl]benzyl}amino)propanoic acid

HRID 1950709Notes

Reaction equation

HRID 1950709 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[C:31]([CH3:36])[CH:30]=2)[C:9]#[C:10][C:11]2[CH:27]=[CH:26][C:14]([CH2:15][NH:16][CH2:17][CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])=[CH:13][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[C:31]([CH3:36])[CH:30]=2)[C:9]#[C:10][C:11]2[CH:27]=[CH:26][C:14]([CH2:15][NH:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:13][CH:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67777133HCID 67777133, compound

Product 1

HCID 677774643-({4-[3-(3-Chlorophenyl)-4-(3,4-dimethylphenyl)but-1-yn-1-yl]benzyl}amino)propanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-((4-[3-(3-chlorophenyl)-4-(3,4-dimethylphenyl)but-1-yn-1-yl)benzyl)amino)propanoate in CH2Cl2 (10 mL) was added TFA (1 mL) at room temperature and the mixture was stirred at room temperature for 16 h. The mixture was evaporated under reduced pressure. The residue was diluted with CH2Cl2:MeOH and the mixture was neutralized with NH3:MeOH silica gel was added, concentrated to dryness, then purified by MPLC using MeOH:CH2Cl2 and Compound 3 (129 mg).

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. additionThe residue was diluted with CH2Cl2
  3. additionMeOH silica gel was added
  4. concentrationconcentrated to dryness
  5. custompurified by MPLC

Sources & evidence

ORD record
ord-8f969d8b641d4f6781cf06f527a38756
Source dataset
uspto-grants-2013_03
Patent number
US08404663B2

Reaction notes

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