Trifluoroacetic acid → (S)-5-chloro-4-((5-chloro-6-((1,1,1-trifluoropropan-2-yl)oxy)pyridin-3-yl)oxy)-2-fluorobenzoic acid

HRID 2048122Notes

Reaction equation

HRID 2048122 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[C:10]([O:23][C:24]2[CH:25]=[N:26][C:27]([O:31][C@@H:32]([CH3:37])[C:33]([F:36])([F:35])[F:34])=[C:28]([Cl:30])[CH:29]=2)=[CH:11][C:12]([F:22])=[C:13]([CH:21]=1)[C:14]([O:16]C(C)(C)C)=[O:15]>ClCCl>[Cl:8][C:9]1[C:10]([O:23][C:24]2[CH:25]=[N:26][C:27]([O:31][C@@H:32]([CH3:37])[C:33]([F:35])([F:36])[F:34])=[C:28]([Cl:30])[CH:29]=2)=[CH:11][C:12]([F:22])=[C:13]([CH:21]=1)[C:14]([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58042393(S)-tert-Butyl 5-chloro-4-((5-chloro-6-((1,1,1-trifluoropropan-2-yl)oxy)pyridin-3-yl)oxy)-2-fluorobenzoate

Product 1

HCID 58042412(S)-5-chloro-4-((5-chloro-6-((1,1,1-trifluoropropan-2-yl)oxy)pyridin-3-yl)oxy)-2-fluorobenzoic acidYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (4.4 mL, 58.7 mmol) was added to a solution of (S)-tert-butyl 5-chloro-4-((5-chloro-6-((1,1,1-trifluoropropan-2-yl)oxy)pyridin-3-yl)oxy)-2-fluorobenzoate (Preparation 298, 9.2 g, 19.6 mmol) in dichloromethane (50 mL). The reaction mixture was stirred at room temperature for 20 hours then concentrated in vacuo. The crude was purified by silica gel chromatography, eluting with heptane:ethyl acetate (from 95:5 to 40:60), to provide the title compound as a white solid (6.9 g, 85%).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe crude was purified by silica gel chromatography
  3. washeluting with heptane

Sources & evidence

ORD record
ord-e6f2712cbdc042aa8b87b0407c80cf35
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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