Water → 2-(3-cyano-5-methoxyphenoxy)-N-(2-methylpent-3-yn-2-yl)-3-methoxypropionamide

HRID 916539ノート

反応式

HRID 916539 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([OH:11])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].Br[CH:19]([CH2:29][O:30][CH3:31])[C:20]([NH:22][C:23]([CH3:28])([CH3:27])[C:24]#[C:25][CH3:26])=[O:21].O>CN(C)C=O.CCCCCC.C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1)[O:11][CH:19]([CH2:29][O:30][CH3:31])[C:20]([NH:22][C:23]([CH3:28])([C:24]#[C:25][CH3:26])[CH3:27])=[O:21])#[N:2]

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 210784052-bromo-3-methoxy-N-(4-methylpent-2-yn-4-yl)propionamideHCID 229962023-Hydroxy-5-methoxybenzonitrile

生成物 1

HCID 691147962-(3-cyano-5-methoxyphenoxy)-N-(2-methylpent-3-yn-2-yl)-3-methoxypropionamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
80 °C

実験手順

3-Cyano-5-methoxyphenol (prepared as described in J. Med. Chem. (1993), 36, No 16, 2367; 0.119 g) in dry N,N-dimethylformamide (3 ml) containing anhydrous potassium carbonate (0.168 g) and 2-bromo-N-(4-methylpent-2-yn-4-yl) 3-methoxypropionamide (0.210 g) were stirred and heated to 80° C. for 5 hours. The mixture was cooled to ambient temperature, stored for 2 days then poured into water and extracted with ethyl acetate. The organic phases were combined, washed with water, dried over magnesium sulphate then evaporated under reduced pressure to give a brown gum. The gum was fractionated by chromatography (silica; hexane/ethyl acetate 3:2 by volume) to give the required product (0.110 g) as a colourless gum.

後処理

  1. temperatureThe mixture was cooled to ambient temperature
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. customthen evaporated under reduced pressure
  6. customto give a brown gum

出典と根拠

ORDレコード
ord-25858ee9eec24a5fb3e45f1f18bc355c
出典データセット
uspto-grants-2007_09
特許番号
US07271130B2

反応ノート

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