O-Xylene → HCID 67686593, compound

HRID 1457262Notes

Reaction equation

HRID 1457262 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[O:14][C@H:10]2[C:11]([NH2:13])=[O:12])=[CH:5][CH:4]=1.C1(C)C(C)=CC=CC=1.[CH3:23][N:24]([CH3:35])[CH2:25][CH2:26][NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[SH:34]>CO>[CH3:23][N:24]([CH3:35])[CH2:25][CH2:26][NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[S:34][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:14])[C:11]([NH2:13])=[O:12]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 10821599HCID 10821599, compoundHCID 10943427Benzenethiol, 2-[[2-(dimethylamino)ethyl]amino]-

Product 1

HCID 67686593HCID 67686593, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (2R,3S)-3-(4-methoxyphenyl)-2,3-epoxypropionamide and xylene is refluxed with heating under nitrogen atmosphere. When the reflux is started, a solution of 2-(2-dimethylaminoethylamino)thiophenol and ferrous sulfate heptahydrate in methanol is added immediately into the reaction mixture, and the mixture is reacted at the same temperature, and cooled to room temperature. The reaction mixture is concentrated under reduced pressure, and the residue is dissolved with heating in ethanol and water. The mixture is allowed to cool to 0° C., and the precipitated crystals are collected by filtration, washed with chilled 50% ethanol, and dried to give (2S,3S)-3-[2-(2-dimethylaminoethylamino)phenylthio]-2-hydroxy-3-(4-methoxyphenyl)propionamide.

Workup

  1. temperatureis refluxed
  2. temperaturewith heating under nitrogen atmosphere
  3. customthe mixture is reacted at the same temperature
  4. concentrationThe reaction mixture is concentrated under reduced pressure
  5. dissolutionthe residue is dissolved
  6. temperaturewith heating in ethanol
  7. temperatureto cool to 0° C.
  8. filtrationthe precipitated crystals are collected by filtration
  9. washwashed
  10. temperaturewith chilled 50% ethanol
  11. customdried

Sources & evidence

ORD record
ord-d4e080623d5641e3b20c4e585b5e1378
Source dataset
uspto-grants-1998_12
Patent number
US05847122

Reaction notes

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