Trifluoroacetic acid → 2-(4-(4-((4-Chlorophenethyl)carbamoyl)phenoxy)-3-cyanophenyl)acetic acid

HRID 453517Notes

Reaction equation

HRID 453517 reaction equation
[Cl:1][C:2]1[CH:35]=[CH:34][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:33]=[CH:32][C:14]([O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25]C(C)(C)C)=[O:24])=[CH:18][C:17]=3[C:30]#[N:31])=[CH:13][CH:12]=2)=[O:10])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]([O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([OH:25])=[O:24])=[CH:18][C:17]=3[C:30]#[N:31])=[CH:32][CH:33]=2)=[O:10])=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68467179tert-Butyl 2-(4-(4-(4-chlorophenethylcarbamoyl)phenoxy)-3-cyanophenyl)acetate

Product 1

HCID 594031942-(4-(4-((4-Chlorophenethyl)carbamoyl)phenoxy)-3-cyanophenyl)acetic acidYield 84.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-cyanophenyl)acetate (4.40 g, 8.96 mmol) in DCM (20 ml) was treated with TFA (20 ml). After stirring for 2 hours. The reaction mixture was concentrated and the crude material was purified by silica gel chromatography using a gradient of 0.5% MeOH/DCM containing 0.5% AcOH to 10% MeOH/DCM containing 0.5% AcOH to provide 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-cyanophenyl)acetic acid (3.30 g, 84.7% yield). 1H NMR (400 MHz, CD3OD) 7.85 (d, 2H), 7.65 (s, 1H), 7.45 (d, 1H), 7.35 (s, 1H), 7.25 (d, 2H), 7.20 (d, 2H), 7.10 (d, 2H), 6.95 (d, 1H), 3.62 (m, 4H), 2.90 (t, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-838ec820c1ed4d78bfaab6bd60c379c3
Source dataset
uspto-grants-2013_07
Patent number
US08492437B2

Reaction notes

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