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Isopropylamine → 3-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid isopropylamide

HRID 1920899
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HRID 1920899 반응식
C[Al](C)C.[CH:5]([NH2:8])([CH3:7])[CH3:6].C[O:10][C:11]([C:13]1[O:17][N:16]=[C:15]([O:18][CH2:19][C:20]2[C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:22][O:23][C:24]=2[CH3:25])[CH:14]=1)=O.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>O1CCOCC1>[CH:5]([NH:8][C:11]([C:13]1[O:17][N:16]=[C:15]([O:18][CH2:19][C:20]2[C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:22][O:23][C:24]=2[CH3:25])[CH:14]=1)=[O:10])([CH3:7])[CH3:6]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6363IsopropylamineHCID 9357Potassium Sodium TartrateHCID 16682925TrimethylaluminumHCID 674922963-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid methyl ester

생성물 1

HCID 468968863-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid isopropylamide수율 74%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

A solution of trimethylaluminium (2 M in toluene, 1.27 mL, 2.6 mmol) was added dropwise (exothermic) to a solution of isopropyl amine (220 μL, 2.6 mmol) in dioxane (6 mL) and the resulting mixture was stirred at room temperature for 30 min. Then 3-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid methyl ester (230 mg, 0.73 mmol) was added. The resulting mixture was then heated at 85-90° C. for 30 min and then cooled to room temperature and then poured into Seignette's salt and extracted with ethyl acetate which was then washed with brine, dried over sodium sulfate and evaporated. Purification by chromatography (silica, heptane:ethyl acetate=4:1 to 0:1) afforded the title compound (184 mg, 74%) which was obtained as a white solid. MS: m/e=342.1 [M+H]+.

후처리

  1. temperatureThe resulting mixture was then heated at 85-90° C. for 30 min
  2. temperaturecooled to room temperature
  3. extractionextracted with ethyl acetate which
  4. washwas then washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customPurification by chromatography (silica, heptane:ethyl acetate=4:1 to 0:1)

출처 및 근거

ORD 기록
ord-3be1e8f5e279485d95293f177684682c
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08173652B2

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