Trifluoroacetic acid → HCID 86703310, compound

HRID 2409993Notes

Reaction equation

HRID 2409993 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([CH2:9][CH:10]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=2[NH:24]C(=O)OC(C)(C)C)[C:11]([CH:13]2[CH2:15][CH2:14]2)=O)[CH:6]=[CH:5][CH:4]=1)#[N:2].FC(F)(F)C(O)=O>C(#N)C.ClCCl>[CH:13]1([C:11]2[NH:24][C:17]3[C:16]([C:10]=2[CH2:9][C:7]2[N:8]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][CH:6]=2)=[CH:21][CH:20]=[C:19]([O:22][CH3:23])[CH:18]=3)[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86703311HCID 86703311, compound

Product 1

HCID 86703310HCID 86703310, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

To a solution of tert-butyl {2-[1-(6-cyanopyridin-2-ylmethyl)-2-cyclopropyl-2-oxoethyl]-5-methoxyphenyl}carbamate (290 mg) in acetonitrile/dichloromethane (2.3 mL/2.3 mL) was added trifluoroacetic acid (2.3 mL) under ice-cooling, and the mixture was stirred at room temperature for 2 days. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and the resulting mixture was washed with a saturated aqueous sodium hydrogen carbonate solution. The organic layer was separated, 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 (189 mg). 1H-NMR (CDCl3) δ ppm: 0.67-0.76 (2H, m), 0.92-1.02 (2H, m), 1.95-2.08 (1H, m), 3.82 (3H, s), 4.35 (2H, s), 6.71 (1H, dd, J=2.3, 8.5 Hz), 6.80 (1H, d, J=2.3 Hz), 7.18-7.29 (2H, m), 7.46-7.52 (1H, m), 7.55-7.68 (2H, m).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe resulting mixture was washed with a saturated aqueous sodium hydrogen carbonate solution
  5. customThe organic layer was separated
  6. washwashed with water and saturated brine successively
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-5e133eacc89e4617ae598e0d9a42f130
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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