Trifluoroacetic acid → HCID 69759657, compound

HRID 1016616Notes

Reaction equation

HRID 1016616 reaction equation
[CH2:1]([O:8][C:9](=[O:24])[NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18]COC)=[C:14]([O:22][CH3:23])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[CH2:1]([O:8][C:9](=[O:24])[NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([O:22][CH3:23])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 69758400HCID 69758400, compound

Product 1

HCID 69759657HCID 69759657, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 13 (0.795 g, 2.4 mmol) in CH2Cl2 (5 mL) was treated with trifluoroacetic acid (2.5 mL) slowly and stirred for 5 min at room temperature. After cooling to 0° C., the reaction mixture was neutralized with saturated NaHCO3 solution, diluted with H2O and extracted with CH2Cl2 several times. The combined organic layer was washed with H2O and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography over silica gel using EtOAc:Hex (2:1) as eluant to give 14 as white solid (680 mg, 99%).

Workup

  1. temperatureAfter cooling to 0° C.
  2. extractionextracted with CH2Cl2 several times
  3. washThe combined organic layer was washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography over silica gel

Sources & evidence

ORD record
ord-01a26617a8364d43ad5c2ac71cdd18ba
Source dataset
uspto-grants-2002_11
Patent number
US06476076B1

Reaction notes

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