HCID 21436323, compound → HCID 21436340, compound

HRID 2397612Notes

Reaction equation

HRID 2397612 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[OH:7][CH:8]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:9][CH2:10][N:11]1[C:15](=[O:16])[CH2:14][S:13][CH:12]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24]>CO.O>[OH:7][CH:8]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:9][CH2:10][N:11]1[C:15](=[O:16])[CH2:14][S:13](=[O:2])[CH:12]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24]

Participants

4

Reactant 2

HCID 21436323HCID 21436323, compoundHCID 23667635Sodium periodate

Product 1

HCID 21436340HCID 21436340, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Sodium metaperiodate (0.75 g., 3.5 millimole) is added to a cold (0°-5° C.) solution of 7-[3-(3-hydroxyoctyl)-4-oxo-2-thiazolidinyl]heptanoic acid (1.24 g., 3.44 millimole) in methanol-water (5:4; v:v; 18 ml.). The resulting mixture is stirred and allowed to slowly warm to 25° C. (as the ice bath melts, etc.) over 16 hours. After removing the precipitated solid via filtration, the filtrate is diluted with cold water and extracted twice with chloroform. The organic extract is washed with saturated aqueous brine, dried over magnesium sulfate, filtered, and evaporated in vacuo leaving an oily residue which is chromatographed on silica gel (20 g.). Elution with chloroform-acetic acid (25:1; v:v) provides the title compound as a viscous, essentially colorless oil.

Workup

  1. customAfter removing the precipitated solid
  2. filtrationvia filtration
  3. additionthe filtrate is diluted with cold water
  4. extractionextracted twice with chloroform
  5. extractionThe organic extract
  6. washis washed with saturated aqueous brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customleaving an oily residue which
  11. customis chromatographed on silica gel (20 g.)
  12. washElution with chloroform-acetic acid (25:1; v:v)

Sources & evidence

ORD record
ord-3b1008912e574048864ac77b42209ece
Source dataset
uspto-grants-1977_05
Patent number
US04022794

Reaction notes

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