Succinic anhydride → N-[5-(1,2-Dithiolan-3-yl)pentyl]succinamic acid

HRID 849572Notes

Reaction equation

HRID 849572 reaction equation
[S:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]2[C:19](=[O:20])[C:18]3[C:13](=CC=CC=3)[C:12]2=[O:21])[S:2]1.C1(=O)OC(=[O:26])CC1>C1(C)C=CC=CC=1.CO.C(N)CCC.N1C=CC=CC=1>[S:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:19](=[O:20])[CH2:18][CH2:13][C:12]([OH:21])=[O:26])[S:2]1

Participants

7

Reactant 2

HCID 7922Succinic anhydrideHCID 183579972-[5-(1,2-Dithiolan-3-yl)pentyl]isoindole-1,3-dione

Product 1

HCID 18358033N-[5-(1,2-Dithiolan-3-yl)pentyl]succinamic acidYield 38%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 1140TolueneSolventHCID 8007ButylamineSolvent

Procedure

The reaction was effected as described in Example 61, but using a solution of 1.5 mmol of 2-[5-(1,2-dithiolan-3-yl)pentyl]isoindole-1,3-dione in 3 ml of toluene, 2 ml of methanol, 2 ml of butylamine, 4 ml of pyridine and 230 mg of succinic anhydride. The solvent was removed from the reaction mixture by distillation under reduced pressure. Water was added to the residue, after which it was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. Ethyl acetate was removed from the extract by distillation under reduced pressure and the residue was subjected to reverse phase preparative silica gel column chromatography, using 2:3, 1:1 and 3:2 by volume mixtures of acetonitrile and water as eluent. Acetonitrile was removed from the eluate so obtained by distillation under reduced pressure. The residue was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. Ethyl acetate was removed from the extract by distillation under reduced pressure. The residue was dissolved in dioxane, after which it was lyophilised, to give 166 mg of the title compound as a pale yellow amorphous substance, melting at 74° C.

Workup

  1. customThe solvent was removed from the reaction mixture by distillation under reduced pressure
  2. additionWater was added to the residue
  3. extractionafter which it was extracted with ethyl acetate
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customEthyl acetate was removed from the
  7. extractionextract by distillation under reduced pressure
  8. customAcetonitrile was removed from the eluate
  9. customso obtained by distillation under reduced pressure
  10. extractionThe residue was extracted with ethyl acetate
  11. washThe extract was washed with a saturated aqueous solution of sodium chloride
  12. dry with materialdried over anhydrous sodium sulfate
  13. customEthyl acetate was removed from the
  14. extractionextract by distillation under reduced pressure
  15. dissolutionThe residue was dissolved in dioxane

Sources & evidence

ORD record
ord-7330f5cae4114968ad2dfbbd35661f94
Source dataset
uspto-grants-2000_01
Patent number
US06013663

Reaction notes

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