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

HRID 650975
Notes
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Reaction equation

HRID 650975 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b962dc1729c24ee3b0df2e9774fa2363
Source dataset
uspto-grants-2001_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06277849B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes