Trifluoroacetic acid → HCID 58452643, compound

HRID 70673Notes

Reaction equation

HRID 70673 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:12]1[CH:17]=[CH:16][C:15](/[C:18](/[C:37]2[N:42]=[C:41]([O:43]C)[C:40]([C:45]#[N:46])=[CH:39][CH:38]=2)=[CH:19]\[C@H:20]2[CH2:24][CH2:23][C:22](=[O:25])[N:21]2CC2C=CC(OC)=CC=2OC)=[CH:14][CH:13]=1)([CH3:11])([CH3:10])[CH3:9]>C1(OC)C=CC=CC=1>[C:8]([C:12]1[CH:13]=[CH:14][C:15](/[C:18](/[C:37]2[NH:42][C:41](=[O:43])[C:40]([C:45]#[N:46])=[CH:39][CH:38]=2)=[CH:19]\[C@H:20]2[CH2:24][CH2:23][C:22](=[O:25])[NH:21]2)=[CH:16][CH:17]=1)([CH3:11])([CH3:9])[CH3:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67398288HCID 67398288, compound

Product 1

HCID 58452643HCID 58452643, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Conditions

Temperature
85 °C

Procedure

Trifluoroacetic acid (1 mL) was added to a solution of 6-{(E)-1-(4-tert-butylphenyl)-2-[(2R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-2-yl]ethenyl}-2-methoxypyridine-3-carbonitrile (32 mg) in anisole (1 mL), and the mixture was stirred at 85° C. overnight. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→1:5). The resulting compound was dissolved in 1,4-dioxane (1 mL) and 48% hydrobromic acid (1 mL) was added, after which the mixture was stirred at 65° C. for one hour. Saturated aqueous sodium bicarbonate was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:5→chloroform:methanol=5:1) to give the title compound (8 mg, 36%) as a colorless solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→1:5)
  3. dissolutionThe resulting compound was dissolved in 1,4-dioxane (1 mL)
  4. addition48% hydrobromic acid (1 mL) was added
  5. stirringafter which the mixture was stirred at 65° C. for one hour
  6. additionSaturated aqueous sodium bicarbonate was added to the reaction solution
  7. extractionfollowed by extraction with ethyl acetate
  8. washThe organic layer was washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customafter which the solvent was evaporated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:5→chloroform:methanol=5:1)

Sources & evidence

ORD record
ord-ed7f9f441dea45f29eb37473cb45ca0f
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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