O-Xylene → HCID 57223133, compound

HRID 1457256Notes

Reaction equation

HRID 1457256 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[O:15][C@H:10]2[C:11]([NH:13][CH3:14])=[O:12])=[CH:5][CH:4]=1.C1(C)C(C)=CC=CC=1.[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[SH:31]>CO>[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31][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:15])[C:11]([NH:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 87132-AminothiophenolHCID 57212777HCID 57212777, compound

Product 1

HCID 57223133HCID 57223133, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (2R,3S)-3-(4-methoxyphenyl)-2,3-epoxy-N-methylpropionamide (829 mg) and xylene (10 ml) is refluxed with heating under nitrogen atmosphere. When the reflux is started, a solution of 2-aminothiophenol (551 mg) and anhydrous ferric chloride (0.065 mg) in methanol (0.08 ml) is added immediately into the reaction mixture, and the mixture is reacted at the same temperature for 5 minutes, and cooled to room temperature. The precipitated crystals are collected by filtration, washed with xylene, and dried at 60° C. to give (2S,3S)-3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)-N-methylpropionamide (1.06 g).

Workup

  1. temperatureis refluxed
  2. temperaturewith heating under nitrogen atmosphere
  3. customthe mixture is reacted at the same temperature for 5 minutes
  4. filtrationThe precipitated crystals are collected by filtration
  5. washwashed with xylene
  6. customdried at 60° C.

Sources & evidence

ORD record
ord-768fcba8ce954c978bc4ab04dd6ae1d2
Source dataset
uspto-grants-1998_12
Patent number
US05847122

Reaction notes

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