Glutaric Acid → HCID 10587290, compound

HRID 1983969Notes

Reaction equation

HRID 1983969 reaction equation
[CH3:1][C:2]1[C:3](=[O:13])[C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.C(O)(=O)[CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19].CC#N.O>[N+]([O-])([O-])=O.[Ag+].C(OCC)(=O)C>[C:18]([CH2:17][CH2:16][CH2:15][C:11]1[C:10](=[O:12])[C:9]2[C:4]([C:3](=[O:13])[C:2]=1[CH3:1])=[CH:5][CH:6]=[CH:7][CH:8]=2)([OH:20])=[O:19]

Participants

7

Reactant 4

HCID 743Glutaric AcidHCID 962WaterHCID 4055MenadioneHCID 6342Acetonitrile2×

Product 1

HCID 10587290HCID 10587290, compound

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The CPVK3 was synthesized referring to a document (Salmon-Chemin L., Buisine E., Yardley V., Kohler S., Debreu M. A., Landry V., Sergheraert C., Croft S. L., Krauth-Siegel R. L., and Davioud-Charvet E., J. Med. Chem., 2001, 44, 548-565). 2-methyl-1,4-naphthoquinone, glutaric acid, and AgNO3 were suspended in a 30% aqueous CH3CN solution, heated, and stirred to dissolve completely. Then, a 30% aqueous CH3CN solution of (NH4)2S2O8 was added dropwise in 60 minutes. After completing the dropwise addition, the mixture was stirred at 65° C. for 5 minutes as it was. Cooling of the reaction mixture to room temperature resulted in precipitation of a yellow brown solid. Water and ethyl acetate were added to the reaction mixture, and an organic layer was washed with water using a separating funnel. Further, the organic layer was washed with water. A 2N-aqueous solution of sodium bicarbonate was added to the organic layer, and a sodium salt of a target compound was extracted to an aqueous layer. Then, the aqueous layer was adjusted to a pH of 2 or less using 37% hydrochloric acid, and a precipitated solid was collected by filtration. The solid was sufficiently washed with cool water, and dried under reduced pressure, to thereby obtain a yellow brown powder 2-(3-carboxypropyl)-3-methyl-1,4-naphthoquinone.

Workup

  1. customThe CPVK3 was synthesized
  2. temperatureheated
  3. dissolutionto dissolve completely
  4. additionthe dropwise addition
  5. stirringthe mixture was stirred at 65° C. for 5 minutes as it
  6. customresulted in precipitation of a yellow brown solid
  7. washan organic layer was washed with water using a separating funnel
  8. washFurther, the organic layer was washed with water
  9. additionA 2N-aqueous solution of sodium bicarbonate was added to the organic layer
  10. extractiona sodium salt of a target compound was extracted to an aqueous layer
  11. filtrationa precipitated solid was collected by filtration
  12. washThe solid was sufficiently washed with cool water
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-cd939e5898b645b2864d22fb61b31a66
Source dataset
uspto-grants-2009_06
Patent number
US07544438B2

Reaction notes

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