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

HRID 1927748Notes

Reaction equation

HRID 1927748 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-27e5a8f0bf224b4194d655ad9c97858b
Source dataset
uspto-grants-2012_05
Patent number
US08183289B2

Reaction notes

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