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2-Chloro-N,N-dimethylethylamine → HCID 67686593, compound

HRID 1457261
Notes
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Reaction equation

HRID 1457261 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14][C@@H:15]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)[C@@H:16]([OH:20])[C:17]([NH2:19])=[O:18].[CH3:29][N:30]([CH3:34])[CH2:31][CH2:32]Cl>CS(C)=O>[CH3:29][N:30]([CH3:34])[CH2:31][CH2:32][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14][C@@H:15]([C:21]1[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)[C@@H:16]([OH:20])[C:17]([NH2:19])=[O:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 11430Potassium CarbonateHCID 10829366(2S,3S)-3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propionamide

Product 1

HCID 67686593HCID 67686593, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

Potassium carbonate is added to dimethyl sulfoxide, and the mixture is stirred at 70° C. The mixture is cooled to room temperature, and thereto is added (2S,3S)-3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propionamide, and stirred. To the reaction mixture is added dropwise 2-dimethylaminoethyl chloride, and the mixture is stirred at room temperature. The reaction mixture is poured into ice-water, and extracted with ethyl acetate. The extract is dried, and concentrated under reduced pressure to remove the solvent to give (2S,3S)-3-[2-(2-dimethylaminoethylamino)phenylthio]-2-hydroxy-3-(4-methoxyphenyl)-propionamide.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. stirringstirred
  3. stirringthe mixture is stirred at room temperature
  4. extractionextracted with ethyl acetate
  5. customThe extract is dried
  6. concentrationconcentrated under reduced pressure
  7. customto remove the solvent

Sources & evidence

ORD record
ord-6fb6628c22094f1baaa5f9e197c8d6e3
Source dataset
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05847122

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes