Trifluoroacetic acid → 4-((E)-3-cyclohexyl-1-propenyl)-2-(4-fluoroanilino)benzoic acid

HRID 2191722Notes

Reaction equation

HRID 2191722 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([CH2:14]/[CH:15]=[CH:16]/[C:17]2[CH:29]=[CH:28][C:20]([C:21]([O:23]C(C)(C)C)=[O:22])=[C:19]([NH:30][C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[CH:18]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>>[CH:8]1([CH2:14]/[CH:15]=[CH:16]/[C:17]2[CH:29]=[CH:28][C:20]([C:21]([OH:23])=[O:22])=[C:19]([NH:30][C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[CH:18]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68964903HCID 68964903, compound

Product 1

HCID 576677964-((E)-3-cyclohexyl-1-propenyl)-2-(4-fluoroanilino)benzoic acid

Procedure

Trifluoroacetic acid 15 mL solution of the obtained tert-butyl 4-((E)-3-cyclohexyl-1-propenyl)-2-(4-fluoroanilino)benzoate was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure, and the obtained residue was refined by reversed-phase silica gel column chromatography [eluent; 70-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution] to give 4-((E)-3-cyclohexyl-1-propenyl)-2-(4-fluoroanilino)benzoic acid 23 mg of pale yellow solid.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-dc9d497883ee4147a0a9b5ce1b38c7db
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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