Fumaric Acid → HCID 22715133, compound

HRID 352120Notes

Reaction equation

HRID 352120 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:3]=1[O:4][CH:5]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]1.[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].[Cl:1][C:2]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:3]=1[O:4][CH:5]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:6][CH2:7][CH2:8][N:9]1[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1

Participants

5

Reactant 2

HCID 444972Fumaric AcidHCID 69829475HCID 69829475, compound

Product 1

HCID 22715133HCID 22715133, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

The product from step (a) (0.20 g, 0.42 mmol) was dissolved in 4M hydrogen chloride in dioxan (10 ml) and stirred for 3hat room temperature. The solvent was evaporated and the residue partitioned between ethyl acetate (50 ml) and aqueous saturated sodium bicarbonate solution (50 ml). The layers were separated and the aqueous portion was extracted with ethyl acetate (2×50 ml). The combined organic portions were washed with water (3×30 ml), dried (magnesium sulphate) and evaporated. The residue was dissolved in methanol and treated with one equivalent of fumaric acid, stirred for ten minutes and then the solvent was removed in vacuo. The solid residue was triturated with ethyl acetate and the white solid obtained filtered off and dried to give the title compound (0.10 g, 49%).,

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between ethyl acetate (50 ml) and aqueous saturated sodium bicarbonate solution (50 ml)
  3. customThe layers were separated
  4. extractionthe aqueous portion was extracted with ethyl acetate (2×50 ml)
  5. washThe combined organic portions were washed with water (3×30 ml)
  6. dry with materialdried (magnesium sulphate)
  7. customevaporated
  8. dissolutionThe residue was dissolved in methanol
  9. stirringstirred for ten minutes
  10. customthe solvent was removed in vacuo
  11. customThe solid residue was triturated with ethyl acetate
  12. customthe white solid obtained
  13. filtrationfiltered off
  14. customdried

Sources & evidence

ORD record
ord-a3c7dc4c66cb4f80bb6b4abed17a1654
Source dataset
uspto-grants-2004_06
Patent number
US06743939B2

Reaction notes

Loading…