4-(3-((2-(1-Hydroxycyclohexyl)ethyl)-4-oxo-2-thiazolidinyl)propyl)benzoic acid → 4-{3-[3-[2-(1-Hydroxycyclohexyl)ethyl]-1,4-dioxo-2-thiazolidinyl]propyl}benzoic Acid

HRID 443670Notes

Reaction equation

HRID 443670 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[OH:7][C:8]1([CH2:14][CH2:15][N:16]2[C:20](=[O:21])[CH2:19][S:18][CH:17]2[CH2:22][CH2:23][CH2:24][C:25]2[CH:33]=[CH:32][C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>CO.O>[OH:7][C:8]1([CH2:14][CH2:15][N:16]2[C:20](=[O:21])[CH2:19][S:18](=[O:2])[CH:17]2[CH2:22][CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][C:28]([C:29]([OH:31])=[O:30])=[CH:32][CH:33]=2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 1750274-(3-((2-(1-Hydroxycyclohexyl)ethyl)-4-oxo-2-thiazolidinyl)propyl)benzoic acidHCID 23667635Sodium periodate

Product 1

HCID 234680744-{3-[3-[2-(1-Hydroxycyclohexyl)ethyl]-1,4-dioxo-2-thiazolidinyl]propyl}benzoic Acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium metaperiodate (0.75 g., 3.5 mmoles) is added to a cold (0°-5° C.) solution of 4-{3-[3-[2-(1-hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoic acid (1.33 g., 3.4 mmoles) in methanol (20 ml.) and water (5 ml.). The resulting mixture is stirred without further cooling for 16 hours. The precipitated solid is then removed by filtration. The filtrate is diluted with water and extracted with chloroform. The organic extract is washed with brine, dried over sodium sulfate, and evaporated in vacuo to leave an oily residue which is chromatographed on silica gel (25 g.). Elution with 4% acetic acid in chloroform affords the title compound as a viscous, yellowish oil.

Workup

  1. temperaturewithout further cooling for 16 hours
  2. customThe precipitated solid is then removed by filtration
  3. additionThe filtrate is diluted with water
  4. extractionextracted with chloroform
  5. extractionThe organic extract
  6. washis washed with brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated in vacuo
  9. customto leave an oily residue which
  10. customis chromatographed on silica gel (25 g.)
  11. washElution with 4% acetic acid in chloroform

Sources & evidence

ORD record
ord-48a7563c79754e088bd788d475e5408f
Source dataset
uspto-grants-1981_04
Patent number
US04260771

Reaction notes

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