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]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
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
- temperaturewithout further cooling for 16 hours
- customThe precipitated solid is then removed by filtration
- additionThe filtrate is diluted with water
- extractionextracted with chloroform
- extractionThe organic extract
- washis washed with brine
- dry with materialdried over sodium sulfate
- customevaporated in vacuo
- customto leave an oily residue which
- customis chromatographed on silica gel (25 g.)
- washElution with 4% acetic acid in chloroform
Sources & evidence
- ORD record
- ord-c4bc94c7de1b4ec1a6a43d65e95374c4
- Source dataset
- uspto-grants-1980_09
- Patent number
- US04225609
Linked notes
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