Trifluoroacetic acid → 2-(3-Cyano-4-(4-(phenethylcarbamoyl)phenoxy)phenyl)acetic acid

HRID 453548Notes

Reaction equation

HRID 453548 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:27][C:28]([O:30]C(C)(C)C)=[O:29])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:26])[NH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:12][CH:11]=1)#[N:2].C(O)(C(F)(F)F)=O>ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([CH2:27][C:28]([OH:30])=[O:29])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16](=[O:26])[NH:17][CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:14][CH:15]=1)#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68466922Tert-butyl 2-(3-cyano-4-(4-(phenethylcarbamoyl)phenoxy)phenyl)acetate

Product 1

HCID 594032032-(3-Cyano-4-(4-(phenethylcarbamoyl)phenoxy)phenyl)acetic acidYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(3-cyano-4-(4-(phenethylcarbamoyl)phenoxy)phenyl)acetate 0.120 g) in 2 ml of dichloromethane was added 2 ml of TFA and the reaction was stirred at ambient temperature. After 1 hour the reaction was concentrated and dried under vacuum to give 2-(3-cyano-4-(4-(phenethylcarbamoyl)phenoxy)phenyl)acetic acid (0.100 g). MS −355.3 [M—CO2H].

Workup

  1. concentrationAfter 1 hour the reaction was concentrated
  2. customdried under vacuum

Sources & evidence

ORD record
ord-1c98c9e1ab63489f83e778a759521090
Source dataset
uspto-grants-2013_07
Patent number
US08492437B2

Reaction notes

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