Sodium hydride → HCID 54432167, compound

HRID 849562Notes

Reaction equation

HRID 849562 reaction equation
[CH2:1]1[C@H:5]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O)[S:4][S:3][CH2:2]1.[CH3:13][S:14]([NH2:17])(=[O:16])=[O:15].[H-].[Na+]>CN(C)C=O>[S:3]1[CH2:2][CH2:1][C@H:5]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]([NH:17][S:14]([CH3:13])(=[O:16])=[O:15])=[O:12])[S:4]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 72879MethanesulfonamideHCID 445125(S)-Lipoic acid

Product 1

HCID 54432167HCID 54432167, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

300 mg of (S)-α-lipoic acid were dissolved in 6 ml of anhydrous dimethylformamide, and 276 mg of N,N'-carbonyldiimidazole and 1 ml of anhydrous dimethylformamide were added to the solution, whilst ice-cooling. The mixture was then stirred at room temperature for 1 hour and 30 minutes. At the end of this time, 162 mg of methanesulfonamide and 74 mg of sodium hydride (as a 55% w/w dispersion in mineral oil) were added to the reaction mixture, whilst ice-cooling, and the mixture was stirred at room temperature for 1 hour and then left to stand for 2 days. The solvent was then removed from the reaction mixture by evaporation under reduced pressure, and water was added to the residue thus obtained, after which it was extracted with ethyl acetate. The extraction solution was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was then removed from the extraction solution by evaporation under reduced pressure. The residue thus obtained was purified by silica gel column chromatography, using 1:1 and 3:1 by volume mixtures of ethyl acetate and hexane as eluent. It was then recrystallized form a 1:2 by volume mixture of ethyl acetate and hexane, to obtain 154 mg of the title compound, melting at 91° C. to 92° C.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 1 hour
  4. waitleft
  5. waitto stand for 2 days
  6. customThe solvent was then removed from the reaction mixture by evaporation under reduced pressure, and water
  7. additionwas added to the residue
  8. customthus obtained
  9. extractionafter which it was extracted with ethyl acetate
  10. washThe extraction solution was washed with a saturated aqueous solution of sodium chloride
  11. dry with materialdried over anhydrous sodium sulfate
  12. customThe solvent was then removed from the extraction solution by evaporation under reduced pressure
  13. customThe residue thus obtained
  14. customwas purified by silica gel column chromatography
  15. customIt was then recrystallized form a 1:2
  16. additionby volume mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-24392aaba57945778a899f06db84ebc9
Source dataset
uspto-grants-2000_01
Patent number
US06013663

Reaction notes

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