Trifluoroacetic acid → HCID 57485789, compound

HRID 597988Notes

Reaction equation

HRID 597988 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:13]3[CH2:14][CH:10]([CH2:11][N:12]3C(OC(C)(C)C)=O)[CH2:9][CH:8]=2)[O:4][N:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:13]3[CH2:14][CH:10]([CH2:11][NH:12]3)[CH2:9][CH:8]=2)[O:4][N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57486351HCID 57486351, compound

Product 1

HCID 57485789HCID 57485789, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 4-(3-methyl-5-isoxazolyl)-6-azabicyclo[3.2.1]oct-3-ene-6-carboxylate (80 mg, 0.28 mmol) in 10 mL of dichloromethane was treated with trifluoroacetic acid (2 mL) with ice bath cooling. After stirring 2 h and warming to ambient temperature, the reaction mixture was concentrated to dryness under reduced pressure. The residue was made basic with 10% potassium hydroxide solution and extracted with chloroform (2×10 mL). The extracts were dried over anhydrous sodium sulfate, filtered and concentrated to give the desired product as a viscous oil (30 mg, 58%).

Workup

  1. temperaturecooling
  2. concentrationthe reaction mixture was concentrated to dryness under reduced pressure
  3. extractionextracted with chloroform (2×10 mL)
  4. dry with materialThe extracts were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cc4cb10992674befb0e30d24b8ce7c14
Source dataset
uspto-grants-2011_03
Patent number
US07897611B2

Reaction notes

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