Trifluoroacetic acid → HCID 53864767, compound

HRID 618623Notes

Reaction equation

HRID 618623 reaction equation
[CH3:1][NH:2][C:3](=[O:24])[C@H:4]([CH3:23])[N:5](C(OC(C)(C)C)=O)[C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][NH:2][C:3](=[O:24])[C@H:4]([CH3:23])[NH:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67605395HCID 67605395, compound

Product 1

HCID 53864767HCID 53864767, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Intermediate 5 (12.46 g) in dichloromethane (124 ml) at 0° C. was treated dropwise with neat trifluoroacetic acid (120 ml). The resulting pale yellow solution was allowed to reach room temperature over 48 h. The solvent was subsequently removed and the crude product dissolved in the minimum volume of 1N hydrochloric acid at 0° C. The aqueous phase was extracted with dichloromethane to remove any impurities. The aqueous phase was then taken to pH 8.5, initially using solid sodium bicarbonate and then a few drops of 3N sodium hydroxide. A white precipitate formed which was filtered, and the residue washed with water and dried in vacuo (7.2 g 83%). TLC Rf 0.10 (EtOAc).

Workup

  1. customThe solvent was subsequently removed
  2. dissolutionthe crude product dissolved in the minimum volume of 1N hydrochloric acid at 0° C
  3. extractionThe aqueous phase was extracted with dichloromethane
  4. customto remove any impurities
  5. customA white precipitate formed which
  6. filtrationwas filtered
  7. washthe residue washed with water
  8. customdried in vacuo (7.2 g 83%)

Sources & evidence

ORD record
ord-4485f06b70a943ffa0d1f98567233c13
Source dataset
uspto-grants-1999_09
Patent number
US05955435

Reaction notes

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