2-Phenylisobutyric acid → 2-[4-(4-Chloro-butyryl)-phenyl]-2-methyl-propionic acid pyrrolidineamide

HRID 411900ノート

反応式

HRID 411900 の反応式
[Al+3].[Cl-].[Cl-].[Cl-].[Cl:5][CH2:6][CH2:7][CH2:8][C:9](Cl)=[O:10].[CH3:12][C:13]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:17])[C:14]([OH:16])=[O:15].[N:24]1([C:29]([NH2:31])=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25]1>C(Cl)(Cl)(Cl)Cl>[N:24]1([C:29]([NH2:31])=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25]1.[Cl:5][CH2:6][CH2:7][CH2:8][C:9]([C:21]1[CH:22]=[CH:23][C:18]([C:13]([CH3:17])([CH3:12])[C:14]([OH:16])=[O:15])=[CH:19][CH:20]=1)=[O:10]

参加物

6

反応物 4

HCID 132222-Phenylisobutyric acidHCID 783704-Chlorobutyryl chlorideHCID 1383351-PyrrolidinecarboxamideHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 698946502-[4-(4-Chloro-butyryl)-phenyl]-2-methyl-propionic acid pyrrolidineamide収率 78%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒2 回

実験手順

Add AlCl3 (8.31 g, 62.3 mmol) to carbon tetrachloride (65 mL) under a nitrogen atmosphere at room temperature. Add 4-chlorobutyryl chloride (03.5 mL, 31.2 mmol), stir for 15 minutes and add, by dropwise addition over 15 minutes, a solution of 2-methyl-2-phenyl-propionic acid, pyrrolidineamide (5.64 g, 26.0 mmol) in carbon tetrachloride (60 mL). Stir at room temperature for 17 hours, pour into ice water (100 mL) and separate the layers. Wash the aqueous layer with methylene chloride (2×70 mL), 5% aqueous sodium hydrogen carbonate, combine the organic layers and dry (Na2SO4). Filter, evaporate the filtrate in vacuo and purify by silica gel chromatography (5:2 hexane/ethyl acetate) to give the title compound (6.55 g, 78%) as a light yellow oil.

後処理

  1. additionadd, by dropwise addition over 15 minutes
  2. customseparate the layers
  3. washWash the aqueous layer with methylene chloride (2×70 mL), 5% aqueous sodium hydrogen carbonate
  4. dry with materialdry (Na2SO4)
  5. filtrationFilter
  6. customevaporate the filtrate in vacuo
  7. custompurify by silica gel chromatography (5:2 hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-3d4dbb9a732f462c9ef31a4fd3c3f7b6
出典データセット
uspto-grants-2003_05
特許番号
US06559312B2

反応ノート

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