Triphenylphosphine → [4-(4-Aminobutyl)phenyl]acetic acid

HRID 25116노트

반응식

HRID 25116 반응식
[C:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][N:15]=[N+]=[N-])=[CH:7][CH:6]=1)([OH:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O.C1COCC1>[C:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][NH2:15])=[CH:7][CH:6]=1)([OH:3])=[O:2]

참가 물질

5

반응물 2

HCID 11776Triphenylphosphine2회HCID 22566167[4-(4-Azidobutyl)phenyl]acetic acid

생성물 1

HCID 22397301[4-(4-Aminobutyl)phenyl]acetic acid수율 53.6%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
25 °C

실험 절차

Azide 7 (1.7 g, 7.2 mmol) and triphenylphosphine (1.9 g, 7.2 mmol) were dissolved in a 10% solution of water in THF (66 mL) and stirred overnight at 25° C. Then more triphenylphosphine (0.8 g, 3 mmol) was added and the heating was continued at 60° C. (oil bath) for 6 h. The solvent was removed under reduced pressure and the residue was treated with 2M HCl (100 mL) and extracted with ethyl acetate (2×50 mL). The water fraction was collected and ammonium hydroxide was added until the pH reached approximately 13. The mixture was extracted with ethyl acetate (2×100 mL) then the organic fraction was washed with brine, water and dried with sodium sulfate. Ethyl acetate was removed under reduced pressure to give 0.8 g (53%) of amine 8.

후처리

  1. customwas continued at 60° C.
  2. customfor 6 h
  3. customThe solvent was removed under reduced pressure
  4. additionthe residue was treated with 2M HCl (100 mL)
  5. extractionextracted with ethyl acetate (2×50 mL)
  6. customThe water fraction was collected
  7. additionammonium hydroxide was added until the pH
  8. extractionThe mixture was extracted with ethyl acetate (2×100 mL)
  9. washthe organic fraction was washed with brine, water
  10. dry with materialdried with sodium sulfate
  11. customEthyl acetate was removed under reduced pressure

출처 및 근거

ORD 기록
ord-64ebc3fc6a3d43e28ca14a791fae0024
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858615B2

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