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

HRID 1927792Notes

Reaction equation

HRID 1927792 reaction equation
[Cl:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:34]=[CH:33][C:14]([O:15][C:16]3[CH:21]=[CH:20][C:19]([CH:22]([F:30])[C:23]([O:25]C(C)(C)C)=[O:24])=[CH:18][C:17]=3[C:31]#[N:32])=[CH:13][CH:12]=2)=[O:10])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:34]=[CH:33][C:14]([O:15][C:16]3[CH:21]=[CH:20][C:19]([CH:22]([F:30])[C:23]([OH:25])=[O:24])=[CH:18][C:17]=3[C:31]#[N:32])=[CH:13][CH:12]=2)=[O:10])=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86643294Tert-butyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-cyanophenyl)-2-fluoroacetate

Product 1

HCID 594031652-(4-(4-((4-Chlorophenethyl)carbamoyl)phenoxy)-3-cyanophenyl)-2-fluoroacetic acidYield 103.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A flask was charged with tert-butyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-cyanophenyl)-2-fluoroacetate (0.026 g), 0.5 ml of dichloromethane and 0.2 ml of TFA. The reaction was concentrated, and the residue was dissolved in a minimal amount of dichloromethane and placed under high vacuum to give a solid. The procedure was repeated to give 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-cyanophenyl)-2-fluoroacetic acid (0.024 g) as a tan solid.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionthe residue was dissolved in a minimal amount of dichloromethane
  3. customto give a solid

Sources & evidence

ORD record
ord-210338186db8489686123b1e821bb7e0
Source dataset
uspto-grants-2012_05
Patent number
US08183289B2

Reaction notes

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