Trifluoroacetic acid → HCID 67684386, compound

HRID 2400290Notes

Reaction equation

HRID 2400290 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[CH2:16][CH:17](O)[CH:18]([CH3:21])[CH2:19][CH3:20])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:21][CH:18]([C:17]1[NH:7][C:8]2[C:9]([CH:16]=1)=[CH:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=2)[CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131731724HCID 131731724, compound

Product 1

HCID 67684386HCID 67684386, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl[2-(2-hydroxy-3-methylpentyl)-4-methoxyphenyl]carbamate (2.65 g) in dichloromethane (25 mL) was added trifluoroacetic acid (5 mL) under ice-cooling. This mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure. To the residue were added ethyl acetate and saturated aqueous sodium hydrogen carbonate solution to separate the organic layer. The organic layer was washed with water and saturated brine successively, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. Under an argon atmosphere, the residue was dissolved in N,N-dimethylformamide (30 mL), and then 2-bromomesitylene (1.50 mL), tetrakis(triphenylphosphine) palladium(0) (472 mg), and potassium carbonate (2.25 g) were added thereto. The mixture was stirred overnight at 150° C. The reaction mixture was cooled to room temperature, and then water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (1.46 g). 1H-NMR (CDCl3) δ ppm: 0.91 (3H, t, J=7.4 Hz), 1.32 (3H, d, J=7.0 Hz), 1.55-1.80 (2H, m), 2.75-2.90 (1H, m), 3.84 (3H, s), 6.15-6.20 (1H, m), 6.77 (1H, dd, J=2.4, 8.8 Hz), 7.02 (1H, d, J=2.4 Hz), 7.19 (1H, d, J=8.8 Hz), 7.77 (1H, br s).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionTo the residue were added ethyl acetate and saturated aqueous sodium hydrogen carbonate solution
  4. customto separate the organic layer
  5. washThe organic layer was washed with water and saturated brine successively
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. dissolutionUnder an argon atmosphere, the residue was dissolved in N,N-dimethylformamide (30 mL)
  9. addition2-bromomesitylene (1.50 mL), tetrakis(triphenylphosphine) palladium(0) (472 mg), and potassium carbonate (2.25 g) were added
  10. stirringThe mixture was stirred overnight at 150° C
  11. temperatureThe reaction mixture was cooled to room temperature
  12. additionwater was added
  13. extractionfollowed by extraction with ethyl acetate
  14. washThe organic layer was washed with water and saturated brine successively
  15. dry with materialdried over anhydrous magnesium sulfate
  16. concentrationconcentrated under reduced pressure
  17. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-dc93bffeb796424a913b1d2cdb09d66b
Source dataset
uspto-grants-2014_08
Patent number
US08796247B2

Reaction notes

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