Trifluoroacetic acid → HCID 178522353, compound

HRID 469705Notes

Reaction equation

HRID 469705 reaction equation
C[O:2][C:3]1(OC)[C:9]([NH:10][C:11](=[O:19])[C:12]2[CH:17]=[CH:16][CH:15]=[N:14][C:13]=2[OH:18])=[CH:8][C:7](=[O:20])[CH:6]2[CH:4]1[O:5]2.FC(F)(F)C(O)=O>ClCCl.C(=O)(O)[O-].[Na+]>[O:2]=[C:3]1[C:9]([NH:10][C:11](=[O:19])[C:12]2[CH:17]=[CH:16][CH:15]=[N:14][C:13]=2[OH:18])=[CH:8][C:7](=[O:20])[CH:6]2[CH:4]1[O:5]2

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 178494374HCID 178494374, compound

Product 1

HCID 178522353HCID 178522353, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 6a (50 mg, 0.16 mmol) in anhydrous dichloromethane (2 was slowly added trifluoroacetic acid (0.5 mL) at room temperature. After overnight stirring, LC-MS indicated 27% starting material remained. Additional trifluoroacetic acid (0.5 mL) was added and the reaction mixture was stirred an additional 24 hours, at which time it was judged complete. The solution was cooled in an ice bath and diluted with additional dichloromethane (10 mL) before the slow addition of saturated sodium bicarbonate solution until the stirring mixture was alkaline. The mixture was then partitioned and the organic solvents were removed and rinsed with brine. The aqueous layer was extracted twice with ethyl acetate and the organic layer was washed with brine. All organics were pooled and dried over anhydrous magnesium sulfate before filtration and solvent evaporation, giving 7a as a light-yellow solid (30 mg, 71%). LC-MS indicated 80% purity, and the material was used in the next step without further purification.

Workup

  1. customat room temperature
  2. stirringthe reaction mixture was stirred an additional 24 hours, at which time it
  3. temperatureThe solution was cooled in an ice bath
  4. customThe mixture was then partitioned
  5. customthe organic solvents were removed
  6. washrinsed with brine
  7. extractionThe aqueous layer was extracted twice with ethyl acetate
  8. washthe organic layer was washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate before filtration and solvent evaporation

Sources & evidence

ORD record
ord-1e04b8706a744e2d8510e2557258fb01
Source dataset
uspto-grants-2014_01
Patent number
US08629164B2

Reaction notes

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