Sodium Hydroxide → (S)-2-(ethylsulfonylamino)-3-methyl-butyric acid N-{2-[4-(5-chloro-thiophen-2-yl-methoxy)-3-methoxy-phenyl]-ethyl}-amide

HRID 650972ノート

反応式

HRID 650972 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:22])[C@@H:12]([NH:16][S:17]([CH2:20][CH3:21])(=[O:19])=[O:18])[CH:13]([CH3:15])[CH3:14])=[CH:4][C:3]=1[O:23][CH3:24].[Cl:25][C:26]1[S:27][C:28]([CH2:31]Cl)=[CH:29][CH:30]=1.C[O-].[Na+].[OH-].[Na+]>CO>[Cl:25][C:26]1[S:27][C:28]([CH2:31][O:1][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:22])[C@@H:12]([NH:16][S:17]([CH2:20][CH3:21])(=[O:19])=[O:18])[CH:13]([CH3:14])[CH3:15])=[CH:4][C:3]=2[O:23][CH3:24])=[CH:29][CH:30]=1

参加物

6

反応物 4

HCID 14798Sodium HydroxideHCID 5830792-Chloro-5-(chloromethyl)thiopheneHCID 10942334Sodium MethoxideHCID 54471411(S)-2-(Ethylsulfonylamino)-3-methyl-butyric acid N-[2-(4-hydroxy-3-methoxyphenyl)-ethyl]-amide

生成物 1

HCID 53920692(S)-2-(ethylsulfonylamino)-3-methyl-butyric acid N-{2-[4-(5-chloro-thiophen-2-yl-methoxy)-3-methoxy-phenyl]-ethyl}-amide

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

A mixture of 2.0 g of (S)-2-(ethylsulfonylamino)-3methyl-butyric acid N-[2-(4hydroxy-3-methoxy-phenyl)-ethyl]-amide, 1.2 g of 2-chloro-5-chloromethylthiophene and 12 ml of a 1 M sodium methanolate solution in methanol (prepared beforehand by dissolution of 23 g of sodium in 1 liter of methanol) is heated at reflux in 30 ml of methanol for 16 hours. After cooling, the reaction mixture is introduced into 300 ml of 2N sodium hydroxide solution. Extraction is carried out twice using 400 ml of tert-butyl methyl ether each time. The organic phases are washed once with 100 ml of 2N sodium hydroxide solution and once with 100 ml of saturated sodium chloride solution, dried over magnesium sulfate and concentrated, yielding (S)-2-(ethylsulfonylamino)-3-methyl-butyric acid N-{2-[4-(5-chloro-thiophen-2-yl-methoxy)-3-methoxy-phenyl]-ethyl}-amide, which can be purified by chromatography on silica gel with ethyl acetate/n-hexane 1:1 and recrystallisation from ethyl acetate/n-hexane, m.p. 124-127° C.

後処理

  1. temperatureis heated
  2. temperatureAfter cooling
  3. extractionExtraction
  4. washThe organic phases are washed once with 100 ml of 2N sodium hydroxide solution and once with 100 ml of saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-cb55c3e6c19c4f42b209fb71f4eaa6ce
出典データセット
uspto-grants-2001_08
特許番号
US06277849B1

反応ノート

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