Isopropylamine → 3-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid isopropylamide

HRID 1920927노트

반응식

HRID 1920927 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]([CH2:26][CH2:27][CH2:28][CH3:29])=[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]([CH2:26][CH2:27][CH2:28][CH3:29])=[N:22][O:23][C:24]=2[CH3:25])[CH:14]=1)=[O:10])([CH3:7])[CH3:6]

참가 물질

6

반응물 4

HCID 6363IsopropylamineHCID 9357Potassium Sodium TartrateHCID 16682925TrimethylaluminumHCID 67491973HCID 67491973, 화합물

생성물 1

HCID 594481373-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid isopropylamide수율 93.3%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

A solution of trimethylaluminium (2 M in toluene, 1.02 mL, 2.0 mmol) was added dropwise (exothermic) to a solution of isopropyl amine (121 mg, 2.0 mmol) in dioxane (6 mL) and the resulting mixture was stirred at room temperature for 1 h. Then 3-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid methyl ester (200 mg, 0.68 mmol) was added. The resulting mixture was then heated at 70° C. for 3 h 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 4:1) afforded the title compound (204 mg, 93%) which was obtained as a colourless oil. MS: m/e=322.4 [M+H]+.

후처리

  1. temperatureThe resulting mixture was then heated at 70° C. for 3 h
  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 4:1)

출처 및 근거

ORD 기록
ord-2f4ddf7ddcc14a6bb3e147460dad3fbc
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173652B2

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