HCID 70161742, compound → HCID 22612399, compound

HRID 844070Notes

Reaction equation

HRID 844070 reaction equation
C(OC(=O)[CH:7]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:31])[C:8](=[O:23])[C:9]1[C:10]([O:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[N:11][CH:12]=[CH:13][CH:14]=1)(C)(C)C>FC(F)(F)C(O)=O>[Cl:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[CH2:24][CH2:7][C:8]([C:9]1[C:10]([O:15][C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)=[N:11][CH:12]=[CH:13][CH:14]=1)=[O:23]

Participants

3

Reactant 1

HCID 70161742HCID 70161742, compound

Product 1

HCID 22612399HCID 22612399, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 226 mg (0.496 mmol) a-[(2-Chlorophenyl)methyl]-2-(4-fluorophenoxy)-β-oxo-3-pyridinepropanoic Acid t-Butyl Ester in 5 mL of trifluoroacetic acid was stirred at rt for 4 h. The mixture was evaporated, and the residue was diluted with 5 mL of toluene, heated to reflux for 2 h, and evaporated. The residue was dissolved in 100 mL of EtOAc, washed successively with saturated aqueous sodium hydrogencarbonate solution (1×50 mL) and brine (1×50 mL), dried (Na2SO4), and and evaporated to 125 mg of an oil. Purification by flash chromatography using 40% ether-hexane as eluant yield 120 mg (68% yield) of the title compound as a colorless oil. 1H NMR (CDCl3) d 3.20 (2H, t, J=8 Hz), 3.49 (2H, t, J =8 Hz), 7.06-7.32 (9H, m), 8.19 (1H, dd, J=2.7 Hz), 8.25 (1H, dd, J=2.5 Hz); Thermospray MS (m/e) 356,358 (M++1).

Workup

  1. customThe mixture was evaporated
  2. additionthe residue was diluted with 5 mL of toluene
  3. temperatureheated
  4. temperatureto reflux for 2 h
  5. customevaporated
  6. dissolutionThe residue was dissolved in 100 mL of EtOAc
  7. washwashed successively with saturated aqueous sodium hydrogencarbonate solution (1×50 mL) and brine (1×50 mL)
  8. dry with materialdried (Na2SO4)
  9. customevaporated to 125 mg of an oil
  10. customPurification by flash chromatography

Sources & evidence

ORD record
ord-de4b3f53ecd145c3ae0848afe7eb8ebb
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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