HCID 19360783, compound → HCID 19360787, compound

HRID 377022Notes

Reaction equation

HRID 377022 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[Br:7][C:8]1[CH:9]=[C:10]([N:15]2[C:19](=[O:20])[CH:18]([OH:21])S[CH2:16]2)[CH:11]=[CH:12][C:13]=1[Cl:14]>O.CO.[Ru](Cl)(Cl)Cl>[Br:7][C:8]1[CH:9]=[C:10]([N:15]2[C:19](=[O:20])[CH:18]([OH:21])[O:2][CH2:16]2)[CH:11]=[CH:12][C:13]=1[Cl:14]

Participants

6

Reactant 2

HCID 19360783HCID 19360783, compoundHCID 23667635Sodium periodate

Product 1

HCID 19360787HCID 19360787, compoundYield 15.2%

Reagents, catalysts & solvents 3

HCID 61850Ruthenium trichlorideCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium periodate (14.2 g) was dissolved in water (175 ml) and ruthenium trichloride (0.7 g) added to give a black solution. The solution was stirred during the addition of 3-(3-bromo-4-chlorophenyl)-5-hydroxythiazolidin-4-one (7.85 g) in methanol (35 ml) over 5 min, the reaction vessel was cooled in an ice bath to control the resulting exotherm. The mixture was stirred for 1 hour before quenching with sodium metabisulfite. The mixture was extracted with ethyl acetate and the combined organic extracts washed with aqueous sodium metabisulfite solution and water, then dried (MgSO4). Evaporation of the solvent under reduced pressure gave a gum which was triturated with dichloromethane to give the title compound as a grey solid (1.13 g), m.p. 139-140° C.

Workup

  1. customto give a black solution
  2. temperaturethe reaction vessel was cooled in an ice bath
  3. custombefore quenching with sodium metabisulfite
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe combined organic extracts washed with aqueous sodium metabisulfite solution and water
  6. dry with materialdried (MgSO4)
  7. customEvaporation of the solvent under reduced pressure
  8. customgave a gum which
  9. customwas triturated with dichloromethane

Sources & evidence

ORD record
ord-2820f19a123349f88f61c50c1c596b83
Source dataset
uspto-grants-2000_02
Patent number
US06022976

Reaction notes

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