Triethylamine → Ethyl 4-(3-acetamidopyrrolidin-1-yl)-2,3,5,6-tetrafluorobenzoylacetate

HRID 1108952Notes

Reaction equation

HRID 1108952 reaction equation
[C:1]([NH:4][CH:5]1[CH2:9][CH2:8][NH:7][CH2:6]1)(=[O:3])[CH3:2].C(N(CC)CC)C.[F:17][C:18]1[C:31]([F:32])=[C:30](F)[C:29]([F:34])=[C:28]([F:35])[C:19]=1[C:20]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:21]>N1C=CC=CC=1>[C:1]([NH:4][CH:5]1[CH2:9][CH2:8][N:7]([C:30]2[C:29]([F:34])=[C:28]([F:35])[C:19]([C:20]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:21])=[C:18]([F:17])[C:31]=2[F:32])[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5227153-AcetamidopyrrolidineHCID 2760255Ethyl (pentafluorobenzoyl)acetate

Product 1

HCID 19957204Ethyl 4-(3-acetamidopyrrolidin-1-yl)-2,3,5,6-tetrafluorobenzoylacetateYield 93.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To 2.62 g (20.4 mmol) of 3-acetamidopyrrolidine dissolved in 50 mL of pyridine and cooled to 0° C. was added 2.06 g (20.4 mmol) of triethylamine and 5.24 g (18.6 mmol) of ethyl 2,3,4,5,6-pentafluorobenzoylacetate, from step 2 above. The solution was stirred at 0° C. for 1 hour, then at room temperature overnight. The solvent was removed by evaporation under vacuum and the residue was dissolved in chlorform, which was washed with 0.5N HCl and 5% potassium carbonate solution. The organic layer was dried over magnesium sulfate, filtered, and evaporated. The residue was further dried by adding and distilling off ethylene dichloride, chloroform and methylene, followed by further drying under vacuum. The crystalline residue was washed with hexane and dried to afford 6.8 g of the title compound as a tan solid, mp 90°-92° C. MS M/Z: 391 (M+H). IR (CDCl3): 1635, 1680, 1740 cm-1. NMR (CDCl3) d: 1.26 (m, 3H), 2.00 (m, 5H), 2.22 (m, 2H), 3.54 (m,1H), 3.77 (m, 2H), 3.85 (m, 1H), 3.98 (m, 1H), 4.22 (m, 2H), 5.75 (m, 1H). Analysis calculated for C17H18F4N2O4 : C, 52.31; H, 4.65; N, 7.18. Found: C, 52.47; H, 4.67; N, 7.33.

Workup

  1. customat room temperature
  2. customovernight
  3. customThe solvent was removed by evaporation under vacuum
  4. dissolutionthe residue was dissolved in chlorform
  5. washwhich was washed with 0.5N HCl and 5% potassium carbonate solution
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was further dried
  10. additionby adding
  11. distillationdistilling off ethylene dichloride, chloroform and methylene
  12. customby further drying under vacuum
  13. washThe crystalline residue was washed with hexane
  14. customdried

Sources & evidence

ORD record
ord-7951464d99024689b1ab10865d660bb2
Source dataset
uspto-grants-1994_06
Patent number
US05318965

Reaction notes

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