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Triethylamine → 3-(4-{[4'-(2-Ethoxyethoxy)-2',6'-dimethylbiphenyl-3-yl]methoxy}-2-fluorophenyl)propanamide

HRID 273406
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HRID 273406 반응식
[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30](O)=[O:31])=[C:24]([F:33])[CH:23]=3)[CH:15]=2)=[C:9]([CH3:34])[CH:8]=1)[CH3:2].N.CO.Cl.C([N:41]=C=NCCCN)C.ON1C2C=CC=CC=2N=N1.C1CCN2C(=NCCC2)CC1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C(#N)C>[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([NH2:41])=[O:31])=[C:24]([F:33])[CH:23]=3)[CH:15]=2)=[C:9]([CH3:34])[CH:8]=1)[CH3:2]
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참가 물질

9

반응물 7

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516892Sodium BicarbonateHCID 129055561-Ethyl-3-(3-aminopropyl)carbodiimide hydrochlorideHCID 21705897Ammonia methanol
HCID 57413373
3-(4-{[4'-(2-Ethoxyethoxy)-2',6'-dimethylbiphenyl-3-yl]methoxy}-2-fluorophenyl)propanoic acid

생성물 1

HCID 589031103-(4-{[4'-(2-Ethoxyethoxy)-2',6'-dimethylbiphenyl-3-yl]methoxy}-2-fluorophenyl)propanamide수율 80%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 3-(4-{[4′-(2-ethoxyethoxy)-2′,6′-dimethylbiphenyl-3-yl]methoxy}-2-fluorophenyl)propanoic acid (0.233 g, 0.500 mmol), 7 M ammonia/methanol (0.4 mL, 2.80 mmol) solution, 1-ethyl-3-(3-aminopropyl)carbodiimide hydrochloride (2.88 g, 1.50 mmol), 1-hydroxybenzotriazole (0.230 g, 1.50 mmol), 1,8-diazabicyclo[5.4.0]-7-undecene (0.448 mL, 3.00 mmol), triethylamine (0.502 mL, 3.60 mmol) and acetonitrile (3 mL) was stirred at room temperature for 27 hrs. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (50% ethyl acetate/hexane-ethyl acetate) to give the title compound (0.186 g, yield 80%) as a colorless oil.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (50% ethyl acetate/hexane-ethyl acetate)

출처 및 근거

ORD 기록
ord-3d1ae8904cff4f2b9eba5ff073760489
출처 데이터셋
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07456218B2

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