Trifluoroacetic acid → HCID 15549971, compound

HRID 844232Notes

Reaction equation

HRID 844232 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O.[CH3:15][N:16]([CH2:18][CH2:19][N:20]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([C:29]3[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=3)[CH:27]=2)[CH:22]=[CH:21]1)[CH3:17]>C(O)(=O)C>[C:1]1([C:22]2[C:23]3[C:28](=[CH:27][C:26]([C:29]4[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=4)=[CH:25][CH:24]=3)[N:20]([CH2:19][CH2:18][N:16]([CH3:17])[CH3:15])[CH:21]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7967CyclohexanoneHCID 15549970HCID 15549970, compound

Product 1

HCID 15549971HCID 15549971, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
110 °C

Procedure

In a 20 mL vial equipped with a screw cap and a stir bar was added cyclohexanone (0.1 mL; 0.88 mmol), trifluoroacetic acid (1 mL) and acetic acid (0.75 mL). The mixture was heated at 110° C. under argon for 15 minutes. A solution of compound (a), above, (0.07 g; 0.25 mmol) in acetic acid (1 mL) was added. The resulting mixture was stirred for an additional 20 minutes at 110° C. The reaction mixture was quenched with potassium hydroxide (1N) (pH: 10; 80 mL) and extracted with ethyl acetate (30 mL). The organic phase was successively washed with water (3×30 mL), brine (30 mL), dried (sodium sulfate), filtered and solvent was removed in vacuo. The residue was purified by column chromatography on silica gel using chloroform:methanol (95:5) to yield the title compound (0.6 g; 64%). 13C NMR (CDCl3): δ 148.6, 147.8, 138.0, 137.3, 134.5, 131.5, 130.9, 125.9, 123.5, 122.5, 121.8, 118.9, 118.4. 107.8, 45.8, 44.8, 34.2, 28.6, 25.8, 23.2, 22.5.

Workup

  1. customIn a 20 mL vial equipped with a screw
  2. customcap
  3. customThe reaction mixture was quenched with potassium hydroxide (1N) (pH: 10; 80 mL)
  4. extractionextracted with ethyl acetate (30 mL)
  5. washThe organic phase was successively washed with water (3×30 mL), brine (30 mL)
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. customsolvent was removed in vacuo
  9. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-7051f6104b1d4544a98591d0d8d2df1e
Source dataset
uspto-grants-2002_04
Patent number
US06380242B1

Reaction notes

Loading…