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Potassium Carbonate → Methyl 3-{4-[[(2',6'-dimethylbiphenyl-3-yl)methyl](propyl)amino]phenyl}propanoate

HRID 508021
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HRID 508021 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=2)[CH:10]=1.I[CH2:30][CH2:31][CH3:32].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]([CH2:30][CH2:31][CH3:32])[C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:22]=2)[CH:10]=1
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 23157312Methyl 3-(4-{[(2',6'-dimethylbiphenyl-3-yl)methyl]amino}phenyl)propanoate

생성물 1

HCID 23157276Methyl 3-{4-[[(2',6'-dimethylbiphenyl-3-yl)methyl](propyl)amino]phenyl}propanoate수율 89%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

To a solution of methyl 3-(4-{[(2′,6′-dimethylbiphenyl-3-yl)methyl]amino}phenyl)propanoate (0.747 g, 2.00 mmol) and 1-iodopropane (0.585 mL, 6.00 mmol) in N,N-dimethylformamide (3 mL) was added potassium carbonate (0.415 g, 3.00 mmol), and the mixture was stirred under a nitrogen atmosphere at 90° C. for 8 hr. After cooling, the reaction mixture was concentrated under reduced pressure. Water was added to the obtained residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-20% ethyl acetate/hexane) to give the title compound (0.740 g, yield 89%) as a yellow oil.

후처리

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionWater was added to the obtained residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane-20% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-04d1d354a78b40cca415b41771d03e23
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07786165B2

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