Trifluoroacetic acid → HCID 25254295, compound

HRID 333778Notes

Reaction equation

HRID 333778 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13](=[O:38])[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]([CH3:36])[C:23]([OH:35])([C:28]2[CH:33]=[CH:32][N:31]=[C:30]([CH3:34])[CH:29]=2)[C:24]([F:27])([F:26])[F:25])=[C:18]([Cl:37])[CH:17]=1)(C)(C)C>ClCCl.O>[Cl:37][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][C:19]=1[CH:22]([CH3:36])[C:23]([OH:35])([C:28]1[CH:33]=[CH:32][N:31]=[C:30]([CH3:34])[CH:29]=1)[C:24]([F:26])([F:27])[F:25])[O:15][CH2:14][C:13]([OH:38])=[O:12]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 25254294HCID 25254294, compound

Product 1

HCID 25254295HCID 25254295, compoundYield 31.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Under an atmosphere of nitrogen, trifluoroacetic acid (1.5 ml) was added to a solution of {3-chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenoxy}-acetic acid tert-butyl ester (Example 78, 98 mg) in dichloromethane (1.5 ml). The reaction mixture was stirred for 1 h at r.t., and then diluted with water, and extracted (ethyl acetate). The combined organic layers were dried (Na2SO4), filtered, and evaporated. Flash chromatography provided the title compound (27 mg, 31%). MS (m/e)=404.4 (MH+).

Workup

  1. extractionextracted (ethyl acetate)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-0f3728a210514a6fb1045972959e0326
Source dataset
uspto-grants-2014_11
Patent number
US08883786B2

Reaction notes

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