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Hydrochloric Acid → (S)-2-(Ethylsulfonylamino)-3-methyl-butyric acid N-[2-(4-hydroxy-3-methoxyphenyl)-ethyl]-amide

HRID 650975
ノート
印刷プレビュー

反応式

HRID 650975 の反応式
[CH2:1]([S:3]([NH:6][C@@H:7]([CH:11]([CH3:13])[CH3:12])[C:8]([OH:10])=O)(=[O:5])=[O:4])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.Cl.[OH:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][NH2:39])=[CH:33][C:32]=1[O:40][CH3:41].Cl>O1CCCC1>[OH:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][NH:39][C:8](=[O:10])[C@@H:7]([NH:6][S:3]([CH2:1][CH3:2])(=[O:4])=[O:5])[CH:11]([CH3:13])[CH3:12])=[CH:33][C:32]=1[O:40][CH3:41]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 11356256N-ethylsulfonyl-L-valineHCID 119576213-Methoxy-4-hydroxyphenylethylamine hydrochloride

生成物 1

HCID 54471411(S)-2-(Ethylsulfonylamino)-3-methyl-butyric acid N-[2-(4-hydroxy-3-methoxyphenyl)-ethyl]-amide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-20 °C

実験手順

5.1 g of (S)-2-(ethylsulfonylamino)-3-methyl-butyric acid and 5.7 ml of N-methylmorpholine in 200 ml of tetrahydrofuran are cooled, with stirring, to −20° C. 3.15 ml of isobutyl chloroformate are added dropwise thereto. When the addition is complete, the reaction mixture is stirred at −10° C. for 40 minutes. The mixture is again cooled to −20° C. 5.0 g of solid 2-(4-hydroxy-3-methoxy-phenyl)-ethylamine hydrochloride are introduced into the reaction mixture. The reaction mixture is stirred, without cooling, for a further 24 hours, the internal temperature gradually rising to room temperature. The reaction mixture is introduced into 300 ml of 2N hydrochloric acid. Extraction is carried out twice using 500 ml of ethyl acetate each time. The organic phases are washed twice using 100 ml of saturated sodium chloride solution each time, dried over magnesium sulfate and concentrated. The residue is purified by flash chromatography on silica gel with a mixture of ethyl acetate/n-hexane 3: 1, yielding (S)-2-(ethylsulfonylamino)-3methyl-butyric acid N-[2-(4-hydroxy-3-methoxyphenyl)-ethyl]-amide in the form of a colourless oil.

後処理

  1. additionWhen the addition
  2. stirringthe reaction mixture is stirred at −10° C. for 40 minutes
  3. temperatureThe mixture is again cooled to −20° C
  4. stirringThe reaction mixture is stirred
  5. temperaturewithout cooling, for a further 24 hours
  6. customgradually rising to room temperature
  7. extractionExtraction
  8. washThe organic phases are washed twice
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated
  11. customThe residue is purified by flash chromatography on silica gel with a mixture of ethyl acetate/n-hexane 3: 1

出典と根拠

ORDレコード
ord-b962dc1729c24ee3b0df2e9774fa2363
出典データセット
uspto-grants-2001_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06277849B1

反応ノート

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