Hydrochloric Acid → HCID 4078860, compound

HRID 1870466Notes

Reaction equation

HRID 1870466 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][CH2:15][C:16]([OH:18])=[O:17].C([O-])([O-])=O.[K+].[K+].Cl>O>[C:16]([CH2:15][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])([OH:18])=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 11430Potassium CarbonateHCID 220977Bicyclo(2.2.2)oct-5-ene-2,3-dicarboxylic Anhydride

Product 1

HCID 4078860HCID 4078860, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a suspension of bicyclo[2.2.2]oct-5-en-2,3-dicarboxylic anhydride (688 mg, 3.9 mmol) in H2O (10 mL) was added glycine (348 mg, 4.6 mmol), and a solution of K2CO3 (321 mg, 2.3 mmol) in H2O (2 mL). The mixture was heated to reflux temperature and allowed to react for 4 hrs. After cooling to room temperature, the mixture was acidified with conc. HCl until the pH reached 1 and extracted with ethyl acetate (EtOAc). The organic layer was washed with brine and dried over Na2SO4. Removal of the solvent gave a colorless solid which was recrystallized from EtOAc/hexane to yield the product as colorless crystals: 653 mg (72% yield), mp=142° C.

Workup

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

Sources & evidence

ORD record
ord-c911fd8322d64f6da50a7ef777ccc20f
Source dataset
uspto-grants-2000_08
Patent number
US06096811

Reaction notes

Loading…