Trifluoroacetic anhydride → HCID 58158576, compound

HRID 2095759Notes

Reaction equation

HRID 2095759 reaction equation
[NH2:1][C:2](=O)[CH2:3][N:4]1[C:9](=[N:10]S(C2C=CC(C)=CC=2)(=O)=O)[CH:8]=[CH:7][C:6]([O:21][C:22]2[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:38])[O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:24][C:23]=2[F:39])=[CH:5]1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCCC1>[NH2:1][C:2]1[N:10]=[C:9]2[CH:8]=[CH:7][C:6]([O:21][C:22]3[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:38])[O:30][CH2:31][C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)=[CH:24][C:23]=3[F:39])=[CH:5][N:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 86651396HCID 86651396, compound

Product 1

HCID 58158576HCID 58158576, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl (4-{[1-(2-amino-2-oxoethyl)-6-{[(4-methylphenyl)sulfonyl]imino}-1,6-dihydropyridin-3-yl]oxy}-3-fluorophenyl)carbamate (28.0 g, 49.6 mmol) in tetrahydrofuran (280 mL) was added trifluoroacetic acid anhydride (196 mL), and the mixture was stirred at room temperature for 3 hr. The solvent was evaporated under reduced pressure, ethyl acetate/tetrahydrofuran was added to the residue, and the mixture was washed with saturated aqueous sodium hydrogen carbonate and saturated brine in this order, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, ethanol (140 mL) and 4N aqueous sodium hydroxide solution (40 mL) were added to the residue, and the mixture was stirred at room temperature for 4 hr. The solvent was concentrated under reduced pressure to about 1/3, water was added to the residue, and the mixture was extracted with ethyl acetate/tetrahydrofuran. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/methanol=10/0→9/1) to give the title compound (10.0 g, 51%).

Workup

  1. customThe solvent was evaporated under reduced pressure, ethyl acetate/tetrahydrofuran
  2. additionwas added to the residue
  3. washthe mixture was washed with saturated aqueous sodium hydrogen carbonate and saturated brine in this order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was evaporated under reduced pressure, ethanol (140 mL) and 4N aqueous sodium hydroxide solution (40 mL)
  7. additionwere added to the residue
  8. stirringthe mixture was stirred at room temperature for 4 hr
  9. concentrationThe solvent was concentrated under reduced pressure to about 1/3, water
  10. additionwas added to the residue
  11. extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran
  12. washThe organic layer was washed with saturated brine
  13. dry with materialdried over anhydrous magnesium sulfate
  14. filtrationfiltered
  15. customThe solvent was evaporated under reduced pressure
  16. customthe residue was purified by silica gel column chromatography (ethyl acetate/methanol=10/0→9/1)

Sources & evidence

ORD record
ord-347ea5ed47d445539dbcc6eb8900b0df
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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