Chlorobenzene → HCID 57060229, compound

HRID 1457264Notes

Reaction equation

HRID 1457264 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[O:20][C@H:10]2[C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:12])=[CH:5][CH:4]=1.ClC1C=CC=CC=1.[NH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[SH:35]>CO>[NH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[S:35][C@@H:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[C@@H:10]([OH:20])[C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:12]

Participants

5

Reactant 3

HCID 7964ChlorobenzeneHCID 87132-AminothiophenolHCID 57063652HCID 57063652, compound

Product 1

HCID 57060229HCID 57060229, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (2R,3S)-3-(4-methoxyphenyl)-2,3-epoxy-N-phenylpropionamide (539 mg) and chlorobenzene (5 ml) is refluxed with heating under nitrogen atmosphere. When the reflux is started, a solution of 2-aminothiophenol (275 mg) and ferric chloride hexahydrate (0.054 mg) in methanol (0.1 ml) is added immediately to the reaction mixture. The mixture is stirred at the same temperature for 5 minutes, and cooled to room temperature. The precipitated crystals are collected by filtration, washed with chlorobenzene, and dried at 50° C. to give (2S,3S)-3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)-N-phenylpropionamide (582 mg).

Workup

  1. temperatureis refluxed
  2. temperaturewith heating under nitrogen atmosphere
  3. filtrationThe precipitated crystals are collected by filtration
  4. washwashed with chlorobenzene
  5. customdried at 50° C.

Sources & evidence

ORD record
ord-8825a0019ae74d969ff0f0f7454027d2
Source dataset
uspto-grants-1998_12
Patent number
US05847122

Reaction notes

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