Trifluoroacetic acid → HCID 53441883, compound

HRID 220645Notes

Reaction equation

HRID 220645 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]([NH:13]C(=O)OC(C)(C)C)[CH2:10][CH2:11][OH:12].FC(F)(F)C(O)=O>ClCCl>[NH2:13][CH:9]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=1[Cl:1])[CH2:10][CH2:11][OH:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59536873HCID 59536873, compound

Product 1

HCID 53441883HCID 53441883, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Of the compound from Example 85A, 800 mg (2.50 mmol) were dissolved in 20 ml of dichloromethane and admixed at 0° C. with 1.92 ml (25.0 mmol) of trifluoroacetic acid, then stirred at room temperature for 1 hour. The mixture was freed from the solvent and from the trifluoroacetic acid on a rotary evaporator. The crude product was taken up in 20 ml of toluene and again concentrated on a rotary evaporator under reduced pressure. Purification took place by chromatography on silica gel. By elution with ethyl acetate it was possible to separate off apolar impurities. Elution with dichloromethane/methanol/26% strength ammonia solution (10:1:0.1) gave 673 mg (79% of theory) of the target compound.

Workup

  1. customThe mixture was freed from the solvent and from the trifluoroacetic acid on a rotary evaporator
  2. concentrationagain concentrated on a rotary evaporator under reduced pressure
  3. customPurification
  4. washBy elution with ethyl acetate it
  5. customto separate off apolar impurities
  6. washElution with dichloromethane/methanol/26% strength ammonia solution (10:1:0.1)
  7. customgave 673 mg (79% of theory) of the target compound

Sources & evidence

ORD record
ord-a74aa38bd7be4a3785d5aa641bdb5efa
Source dataset
uspto-grants-2012_06
Patent number
US08202895B2

Reaction notes

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