Lipoic acid → (r)-n-[5-(1,2-Dithiolan-3-yl)pentanoyl]methanesulfonamide

HRID 849563

反応式

HRID 849563 の反応式
[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

参加物

5

反応物 3

HCID 6112Lipoic acidHCID 24758Sodium hydrideHCID 72879Methanesulfonamide

生成物 1

HCID 54432166(r)-n-[5-(1,2-Dithiolan-3-yl)pentanoyl]methanesulfonamide収率 45%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

110 mg of (R)-α-lipoic acid were dissolved in 2 ml of anhydrous dimethylformamide, and 97 mg of N,N'-carbonyldiimidazole were added to the solution, whilst ice-cooling. The mixture was then stirred at room temperature for 4 hours. At the end of this time, 57 mg of methanesulfonamide and 26 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 5 hours and then left to stand overnight. The solvent was then removed from the reaction mixture by evaporation under reduced pressure, and water was added to the residue this obtained. The resulting mixture was neutralized by the addition of 2 N aqueous hydrochloric acid, after which it was extracted with ethyl acetate. The extraction solution was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. The solvent was 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, after which it was dissolved in dioxane and lyophilised, to obtain 68 mg of the title compound, melting at 71° C. to 73° C.

後処理

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 5 hours
  4. waitleft
  5. waitto stand overnight
  6. customThe solvent was then removed from the reaction mixture by evaporation under reduced pressure, and water
  7. additionwas added to the residue this obtained
  8. additionThe resulting mixture was neutralized by the addition of 2 N aqueous hydrochloric acid
  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 removed from the extraction solution by evaporation under reduced pressure
  13. customThe residue thus obtained
  14. customwas purified by silica gel column chromatography
  15. dissolutionafter which it was dissolved in dioxane

出典と根拠

ORDレコード
ord-cac56cd32e1d4e86b73d04226b950141
出典データセット
uspto-grants-2000_01
特許番号
US06013663

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