Trifluoroacetic acid → HCID 59434151, compound

HRID 508104Notes

Reaction equation

HRID 508104 reaction equation
[O:1]=[S:2]1(=[O:42])[CH2:7][CH2:6][CH:5]([CH2:8][O:9][C:10]2[CH:15]=[C:14]([CH3:16])[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][NH:24][C:25]4[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][C:33]([O:35]C(C)(C)C)=[O:34])=[C:27]([F:40])[CH:26]=4)[CH:18]=3)=[C:12]([CH3:41])[CH:11]=2)[CH2:4][CH2:3]1.FC(F)(F)C(O)=O>C(Cl)Cl>[O:42]=[S:2]1(=[O:1])[CH2:7][CH2:6][CH:5]([CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH3:41])[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][NH:24][C:25]4[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[C:27]([F:40])[CH:26]=4)[CH:18]=3)=[C:14]([CH3:16])[CH:15]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59434148HCID 59434148, compound

Product 1

HCID 59434151HCID 59434151, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl 3-{4-[({4′-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)methoxy]-2′,6′-dimethylbiphenyl-3-yl}methyl)amino]-2-fluorophenyl}propanoate (0.08 g, 0.14 mmol) in methylene chloride (2 mL) was added trifluoroacetic acid (2 mL) under stirring at 0° C., and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was neutralized with saturated aqueous sodium hydrogencarbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give the title compound (0.06 g, yield 78%) as colorless crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-7ed7a022f0d0436a83fea76cd1c52d5c
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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