Fumaric Acid → HCID 69802605, compound

HRID 2179970Notes

Reaction equation

HRID 2179970 reaction equation
CC(OC(=O)[NH:7][CH2:8][CH2:9][C@@H:10]([O:16][C:17]1[CH:22]=[C:21]([Cl:23])[C:20]([F:24])=[CH:19][C:18]=1[C:25]#[N:26])[C:11]1[CH:15]=[CH:14][O:13][CH:12]=1)(C)C.C(=O)(O)[O-].[Na+].[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37]>Cl.O1CCOCC1>[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37].[NH2:7][CH2:8][CH2:9][C@@H:10]([O:16][C:17]1[CH:22]=[C:21]([Cl:23])[C:20]([F:24])=[CH:19][C:18]=1[C:25]#[N:26])[C:11]1[CH:15]=[CH:14][O:13][CH:12]=1

Participants

6

Reactant 3

HCID 444972Fumaric AcidHCID 516892Sodium BicarbonateHCID 70153777HCID 70153777, compound

Product 1

HCID 69802605HCID 69802605, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

The product from step (c) (150 mg, 0.3 mmol) was dissolved in 4M HCl in dioxan (10 ml) and stirred at room temperature for 10 minutes. The reaction was placed in an ice-bath and aqueous saturated sodium bicarbonate solution (30 ml) added cautiously. The mixture wa extracted with ethyl acetate (3×50 ml) and the combined extracts were washed with water (20 ml), dried (sodium sulphate) and evaporated in vacuo. The residue was chromatographed on flash silica, eluting with 5% 7N ammonia in methanol in dichloromethane. The product was dissolved in methanol (5 ml) and treated with one equivalent of fumaric acid. Stirred for 10 minutes then removed the solvent in vacuo and triturated the solid residue with a little ethyl acetate. The white solid was filtered off and dried to give the title compound (50 mg, 40%).

Workup

  1. customThe reaction was placed in an ice-bath
  2. extractionThe mixture wa extracted with ethyl acetate (3×50 ml)
  3. washthe combined extracts were washed with water (20 ml)
  4. dry with materialdried (sodium sulphate)
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on flash silica
  7. washeluting with 5% 7N ammonia in methanol in dichloromethane
  8. dissolutionThe product was dissolved in methanol (5 ml)
  9. stirringStirred for 10 minutes
  10. customthen removed the solvent in vacuo
  11. customtriturated the solid residue with a little ethyl acetate
  12. filtrationThe white solid was filtered off
  13. customdried

Sources & evidence

ORD record
ord-a6110054b8a8423fa45c71469dc646a4
Source dataset
uspto-grants-2005_05
Patent number
US06887871B2

Reaction notes

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