Trifluoroacetic acid → HCID 86624379, compound

HRID 508064Notes

Reaction equation

HRID 508064 reaction equation
[CH2:1]([S:3]([CH2:6][CH2:7][O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][NH:23][C:24]3[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]([O:34]C(C)(C)C)=[O:33])=[C:26]([F:39])[CH:25]=3)[CH:17]=2)=[C:11]([CH3:40])[CH:10]=1)(=[O:5])=[O:4])[CH3:2].FC(F)(F)C(O)=[O:44]>C1(C)C=CC=CC=1.C(OCC)(=O)C.CS(O)(=O)=O>[CH3:6][S:3]([OH:4])(=[O:5])=[O:44].[CH2:1]([S:3]([CH2:6][CH2:7][O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][NH:23][C:24]3[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[C:26]([F:39])[CH:25]=3)[CH:17]=2)=[C:11]([CH3:40])[CH:10]=1)(=[O:4])=[O:5])[CH3:2]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23157602HCID 23157602, compound

Product 1

HCID 86624379HCID 86624379, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6395Methanesulfonic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl 3-{4-[({4′-[2-(ethylsulfonyl)ethoxy]-2′,6′-dimethylbiphenyl-3-yl}methyl)amino]-2-fluorophenyl}propanoate (1.17 g, 2.05 mmol) in toluene (20 mL) was added trifluoroacetic acid (20 mL) under stirring at 0° C., and the mixture was stirred at room temperature for 1.5 hr. The reaction mixture was concentrated under reduced pressure, the residue was neutralized with saturated aqueous sodium hydrogencarbonate, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1-hexane/ethyl acetate=1/4) to give a colorless oil. The obtained oil was diluted with ethyl acetate, and methanesulfonic acid (0.12 mL) was added. The precipitated crystals were collected by filtration, washed and dried to give the title compound (1.00 g, yield 80%) as colorless crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 1.5 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1-hexane/ethyl acetate=1/4)
  8. customto give a colorless oil
  9. additionwas added
  10. filtrationThe precipitated crystals were collected by filtration
  11. washwashed
  12. customdried

Sources & evidence

ORD record
ord-ba8228b2109f42c18b0ee2710f19222e
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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