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

HRID 636889
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HRID 636889 반응식
[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.C(OC(Cl)=O)C(C)C.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]
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참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-20 °C

실험 절차

5.1 g of (S)-2-(ethylsulfonylamino)-3-methyl-butyric acid and 5.7 ml of N-methylmorpholine are cooled in 200 ml of tetrahydrofuran, with stirring, to −20° C. 3.15 ml of chloroformic acid isobutyl ester are added dropwise thereto. Stirring is then carried out for 30 min, during which the reaction temperature is increased to −10° C. Cooling is then carried out to −20° C. again and 5.0 g of 2-(4-hydroxy-3-methoxyphenyl)-ethylamine hydrochloride are introduced. The reaction mixture is allowed to warm to room temperature and is stirred for a further 24 hours. The reaction mixture is introduced into 300 ml of 2N hydrochloric acid. It is extracted twice with 500 ml of ethyl acetate each time. The organic phases are washed twice with 100 ml of saturated sodium chloride solution each time, combined, dried over magnesium sulfate and concentrated. The residue is purified by flash-chromatography on silica gel using a mixture of ethyl acetate/n-hexane 3:1, yielding (S)-2-(ethylsulfonylamino)-3-methyl-butyric acid N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-amide in the form of a colourless oil.

후처리

  1. stirringStirring
  2. temperaturethe reaction temperature is increased to −10° C
  3. temperatureCooling
  4. customis then carried out to −20° C.
  5. temperatureto warm to room temperature
  6. stirringis stirred for a further 24 hours
  7. extractionIt is extracted twice with 500 ml of ethyl acetate each time
  8. washThe organic phases are washed twice with 100 ml of saturated sodium chloride solution each time
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated
  11. customThe residue is purified by flash-chromatography on silica gel using
  12. additiona mixture of ethyl acetate/n-hexane 3:1

출처 및 근거

ORD 기록
ord-aa537a4819054daa85ce54c2f8a1f2bb
출처 데이터셋
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06194611B1

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