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

HRID 1920927ノート

反応式

HRID 1920927 の反応式
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]

参加物

6

反応物 4

HCID 6363IsopropylamineHCID 9357Potassium Sodium TartrateHCID 16682925TrimethylaluminumHCID 67491973HCID 67491973、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-2f4ddf7ddcc14a6bb3e147460dad3fbc
出典データセット
uspto-grants-2012_05
特許番号
US08173652B2

反応ノート

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