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

HRID 650972노트

반응식

HRID 650972 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cb55c3e6c19c4f42b209fb71f4eaa6ce
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06277849B1

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