DL-valine → HCID 18696372, compound

HRID 1870469Notes

Reaction equation

HRID 1870469 reaction equation
[CH:1]12[CH2:8][CH2:7][CH:4]([CH:5]=[CH:6]1)[CH:3]1[C:9]([O:11][C:12](=[O:13])[CH:2]21)=O.[NH2:14][CH:15]([C:19]([OH:21])=[O:20])[CH:16]([CH3:18])[CH3:17].C([O-])([O-])=O.[K+].[K+]>O>[C:19]([CH:15]([N:14]1[C:12](=[O:13])[CH:2]2[CH:3]([CH:4]3[CH2:7][CH2:8][CH:1]2[CH:6]=[CH:5]3)[C:9]1=[O:11])[CH:16]([CH3:18])[CH3:17])([OH:21])=[O:20]

Participants

5

Reactant 3

HCID 1182DL-valineHCID 11430Potassium CarbonateHCID 220977Bicyclo(2.2.2)oct-5-ene-2,3-dicarboxylic Anhydride

Product 1

HCID 18696372HCID 18696372, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a suspension of bicyclo[2.2.2]oct-5-en-2,3-dicarboxylic anhydride (2.01 g, 11.3 mmol) in H2O (25 mL) was added (dl)-valine (1.58 g, 13.5 mmol) and a solution of K2CO3 (934 mg, 6.8 mmol) in H2O (3 mL). The mixture was heated to reflux temperature and allowed to react for 4 hrs. After cooling to room temperature, the mixture was washed with EtOAc, acidified with conc. HCl until the pH reached 1 and extracted with EtOAc. The organic layer was washed with 5% HCl followed by brine and then dried over Na2SO4. Removal of the solvent gave a beige solid which was recrystallized from EtOAc/hexane to yield the product as off-white crystals: 1.72 g (55% yield), mp=156° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux temperature
  3. customto react for 4 hrs
  4. washthe mixture was washed with EtOAc
  5. extractionextracted with EtOAc
  6. washThe organic layer was washed with 5% HCl
  7. dry with materialdried over Na2SO4
  8. customRemoval of the solvent
  9. customgave a beige solid which
  10. customwas recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-ac3295f7d3c843eda406875ab3e22eb6
Source dataset
uspto-grants-2000_08
Patent number
US06096811

Reaction notes

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