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

HRID 1108952
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HRID 1108952 반응식
[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]
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7951464d99024689b1ab10865d660bb2
출처 데이터셋
uspto-grants-1994_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05318965

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