Trifluoroacetic acid → HCID 68663591, compound

HRID 452753Notes

Reaction equation

HRID 452753 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([C:14]2[O:15][C:16]([S:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[N:17][N:18]=2)[CH:11]=[CH:10][N:9]=1)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+]>ClCCl>[F:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][S:19][C:16]2[O:15][C:14]([C:12]3[CH:11]=[CH:10][N:9]=[C:8]([NH2:7])[CH:13]=3)=[N:18][N:17]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 86640037HCID 86640037, compound

Product 1

HCID 68663591HCID 68663591, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl[4-[5-[(4-fluorobenzyl)thio]-1,3,4-oxadiazol-2-yl]-2-pyridyl]carbamate (138 mg, 0.343 mmol) in dichloromethane (5 mL) was added trifluoroacetic acid (5 mL), and the resulting mixture was stirred at room temperature for 5 hr. The reaction mixture was alkalified with aqueous sodium hydroxide solution, and the mixture was extracted with chloroform. 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=95/5-0/100), and recrystallized from methanol/chloroform/diethyl ether to give the title compound (44 mg, yield 43%) as colorless crystals.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5-0/100)
  6. customrecrystallized from methanol/chloroform/diethyl ether

Sources & evidence

ORD record
ord-5aca6c7dcad948b188981794d324e0dd
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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