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

HRID 636891
Notes
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Reaction equation

HRID 636891 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].[OH:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][NH2:23])=[CH:17][C:16]=1[O:24][CH3:25].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O.O>[OH:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][NH:23][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:17][C:16]=1[O:24][CH3:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 16693-MethoxytyramineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 11356256N-ethylsulfonyl-L-valine

Product 1

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

Reagents, catalysts & solvents

2
HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.1 g of (S)-2-(ethylsulfonylamino)-3-methyl-butyric acid, 1.7 g of 2-(4-hydroxy-3-methoxyphenyl)-ethylamine, 4.6 g of (benzotriazol-1-yloxy)-tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and 4.5 ml of N,N-diisopropylethylamine is stirred in 40 ml of N,N-dimethylformamide at room temperature for 2 hours. The reaction mixture is introduced into 500 ml of water and extracted twice with 400 ml of ethyl acetate each time. The organic phases are washed once with 300 ml of water and once with 200 ml of saturated sodium chloride solution, dried over magnesium sulfate and concentrated. (S)-2-(Ethylsulfonylamino)-3-methyl-butyric acid N-[2-(4-hydroxy-3-methoxyphenyl)-ethyl]-amide is obtained in the form of an oil, which can be purified by flash-chromatography on silica gel using a mixture of ethyl acetate/n-hexane=3:1.

Workup

  1. extractionextracted twice with 400 ml of ethyl acetate each time
  2. washThe organic phases are washed once with 300 ml of water and once with 200 ml of saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5cd0df630b9f43a48ea3c1469540a03c
Source dataset
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06194611B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes