Methanol → HCID 18358059, compound

HRID 849582Notes

Reaction equation

HRID 849582 reaction equation
CO.C(N)CCC.[S:8]1[CH2:12][CH2:11][CH:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]2C(=O)[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]2=[O:28])[S:9]1>C1(C)C=CC=CC=1>[S:8]1[CH2:12][CH2:11][CH:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:28])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[S:9]1

Participants

5

Reactant 3

HCID 887MethanolHCID 8007ButylamineHCID 183579972-[5-(1,2-Dithiolan-3-yl)pentyl]isoindole-1,3-dione

Product 1

HCID 18358059HCID 18358059, compoundYield 11.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2 ml of methanol and 2 ml of butylamine were added to 3 ml of a solution of 1.6 mmol of 2-[5-(1,2-dithiolan-3-yl)pentyl]isoindoline-1,3-dione (prepared as described in Example 58) in toluene, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was then left to stand at room temperature for 2 days, after which the solvent was removed from the reaction mixture by evaporation under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extraction solution was washed with saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The ethyl acetate was removed from the extraction solution by evaporation under reduced pressure, and 5 ml of anhydrous tetrahydrofuran, 0.33 ml of triethylamine and 0.28 ml of benxoyl chloride were added to the residue. The mixture was then stirred at room temperature for 6 hours. At the end of this time, the solvent was removed from the reaction mixture by evaporation under reduced pressure, and water was added to the residue, 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 ethyl acetate was removed from the extraction solution by evaporation under reduced pressure, and the residue was subjected to silica gel column chromatography, using 1:8, 1:4 and 1:2 by volume mixtures of ethyl acetate and hexane as the eluent. The residue was then subjected to reverse phase preparative silica gel column chromatography, using 2:3 and 1:1 by volume mixtures of acetonitrile and water was eluent, and the acetonitrile was removed from the solution by evaporation under reduced pressure, after which the residue 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 ethyl acetate was removed from the extraction solution by evaporation under reduced pressure, and the residue was dissolved in dioxane and then lyophilised, to obtain 56 mg of the title compound as a yellow amorphous substance, melting at 58 to 59° C.

Workup

  1. waitThe reaction mixture was then left
  2. waitto stand at room temperature for 2 days
  3. customafter which the solvent was removed from the reaction mixture by evaporation under reduced pressure
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extraction solution was washed with saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe ethyl acetate was removed from the extraction solution by evaporation under reduced pressure, and 5 ml of anhydrous tetrahydrofuran, 0.33 ml of triethylamine and 0.28 ml of benxoyl chloride
  9. additionwere added to the residue
  10. stirringThe mixture was then stirred at room temperature for 6 hours
  11. customAt the end of this time, the solvent was removed from the reaction mixture by evaporation under reduced pressure, and water
  12. additionwas added to the residue
  13. extractionafter which it was extracted with ethyl acetate
  14. washThe extraction solution was washed with a saturated aqueous solution of sodium chloride
  15. dry with materialdried over anhydrous sodium sulfate
  16. customThe ethyl acetate was removed from the extraction solution by evaporation under reduced pressure
  17. customthe acetonitrile was removed from the solution by evaporation under reduced pressure
  18. extractionafter which the residue was extracted with ethyl acetate
  19. washThe extraction solution was washed with a saturated aqueous solution of sodium chloride
  20. dry with materialdried over anhydrous sodium sulfate
  21. customThe ethyl acetate was removed from the extraction solution by evaporation under reduced pressure
  22. dissolutionthe residue was dissolved in dioxane

Sources & evidence

ORD record
ord-a3f32e81562c4a1a8901a4aa52719b62
Source dataset
uspto-grants-2000_01
Patent number
US06013663

Reaction notes

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