Sodium Iodide → 4-[4-(1,4,7-Trioxaoct-1-yl)phenyl]-N-benzyloxycarbonylbutylamine

HRID 81314

반응식

HRID 81314 반응식
C([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)(OCC1C=CC=CC=1)=O.Br[CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH3:30].[C:31](=[O:34])([O-])[O-:32].[K+].[K+].[I-].[Na+]>CC(C)=O.CN(C=O)C>[O:22]([C:19]1[CH:18]=[CH:17][C:16]([CH:15]([C:31]([O:32][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:34])[CH2:14][CH2:13][CH2:12][NH2:11])=[CH:21][CH:20]=1)[CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH3:30]

참가 물질

7

반응물 4

HCID 5238Sodium Iodide2회HCID 11430Potassium Carbonate3회HCID 1235321-Bromo-3,6-dioxaheptane3회HCID 11637991N-Cbz4-(4-hydroxyphenyl)butylamine

생성물 1

HCID 673669224-[4-(1,4,7-Trioxaoct-1-yl)phenyl]-N-benzyloxycarbonylbutylamine수율 166%

시약·촉매·용매 2

HCID 180Acetone용매HCID 6228Dimethylformamide용매

실험 절차

4-(4-Hydroxyphenyl)-N-benzyloxycarbonylbutylamine (29) (1.0 g, 3.3 mmol), 1-bromo-2-(2-methoxyethoxy)ethane (0.67 g, 3.7 mmol), and potassium carbonate (0.60 g, 4.3 mmol) were combined in acetone (20 mL), and stirred at reflux overnight. The reaction was allowed to cool, and then filtered and evaporated. The residue was re-subjected in methyl ethyl ketone (10 mL), 1-bromo-2-(2-methoxyethoxy)ethane (0.91 g, 5.0 mmol), potassium carbonate (0.74 g, 5.3 mmol), and sodium iodide (0.5 g, 3.3 mmol) with stirring at reflux for 2.5 h. The reaction was allowed to cool, and was filtered and evaporated. The residue was re-subjected in DMF (10 mL), with 1-bromo-2-(2-methoxyethoxy)ethane (1.8 g, 9.8 mmol), potassium carbonate (1.60 g, 11.6 mmol), and sodium iodide (0.4 g, 2.7 mmol), overnight with stirring at 70° C. The reaction was evaporated to remove the solvent and then was dissolved in ethyl acetate (70 mL). The organic extract was washed with water (3×20 mL), dried over potassium carbonate and filtered. Evaporation afforded 1.1 g of an oil which was purified by column chromatography (silica gel, 2:1 hexanes/ethyl acetate) to afford 800 mg (70%) of pure product 106. 1H NMR (300 MHz, CDCl3) δ 1.42-1.68 (m, 4H), 2.55 (t, J=7.5 Hz, 2H), 3.20 (q, J=6.2 Hz, 2H), 3.39 (s, 3H), 3.55-3.60 (m, 2H), 3.69-3.74 (m, 2H), 3.82-3.87 (m, 2H), 4.11 (t, 5.3 Hz, 2H), 4.71 (br s, 1H), 5.09 (s, 2H), 6.82 (d, J=8.5 Hz, 2H), 7.05 (d, J=8.5 Hz, 2H), 7.34 (s, 5H). CI MS m/z=402 [C23H31NO5+H]+.

후처리

  1. temperatureat reflux overnight
  2. temperatureto cool
  3. filtrationfiltered
  4. customevaporated
  5. temperatureat reflux for 2.5 h
  6. temperatureto cool
  7. filtrationwas filtered
  8. customevaporated
  9. stirringwith stirring at 70° C
  10. customThe reaction was evaporated
  11. customto remove the solvent
  12. dissolutionwas dissolved in ethyl acetate (70 mL)
  13. extractionThe organic extract
  14. washwas washed with water (3×20 mL)
  15. dry with materialdried over potassium carbonate
  16. filtrationfiltered
  17. customEvaporation

출처 및 근거

ORD 기록
ord-bd36345c727043a58258443ebbfadeca
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846688B2

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