Trifluoroacetic acid → HCID 58424842, compound

HRID 2409396Notes

Reaction equation

HRID 2409396 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]2[C:22]3[NH:21][CH2:20][CH2:19][CH2:18][C:17]=3[C:16](=[O:23])[N:15](CC3C=CC(OC)=CC=3)[C:14]=2[CH:33]=1>>[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]2[C:22]3[NH:21][CH2:20][CH2:19][CH2:18][C:17]=3[C:16](=[O:23])[NH:15][C:14]=2[CH:33]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58424962HCID 58424962, compound

Product 1

HCID 58424842HCID 58424842, compoundYield 85.5%

Conditions

Temperature
100 °C

Procedure

Trifluoroacetic acid (2 ml) was added to the compound (102.9 mg, 0.294 mmol) prepared in step 4 and the mixture was stirred in sealed-tube for 20 hours at 100° C. Once the reaction was completed, the reaction mixture was cooled to a room temperature and extracted with dichloromethane. The organic layer was washed with sodium bicarbonate aqueous solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was stirred in ethylacetate/hexane/diethylether and the resulting solid was filtered. The filtered solid was washed with diethylether and dried in vacuo to obtain the title compound (57.8 mg, yield: 85.5%, ivory solid).

Workup

  1. temperaturethe reaction mixture was cooled to a room temperature
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with sodium bicarbonate aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. stirringThe residue was stirred in ethylacetate/hexane/diethylether
  7. filtrationthe resulting solid was filtered
  8. washThe filtered solid was washed with diethylether
  9. customdried in vacuo

Sources & evidence

ORD record
ord-5abddd604a654b9a88d07ab531757592
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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