L-Phenylalanine → HCID 18696371, compound

HRID 1870468Notes

Reaction equation

HRID 1870468 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([O-])([O-])=O.[K+].[K+].[CH:19]12[CH2:26][CH2:25][CH:22]([CH:23]=[CH:24]1)[CH:21]1[C:27]([O:29][C:30](=O)[CH:20]21)=[O:28]>O>[C:10]([CH:2]([N:1]1[C:27](=[O:28])[CH:21]2[CH:20]([CH:19]3[CH2:26][CH2:25][CH:22]2[CH:23]=[CH:24]3)[C:30]1=[O:29])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 6140L-PhenylalanineHCID 11430Potassium CarbonateHCID 220977Bicyclo(2.2.2)oct-5-ene-2,3-dicarboxylic Anhydride

Product 1

HCID 18696371HCID 18696371, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a suspension of L-phenylalanine (502 mg, 3.0 mmol) in H2O (15 mL) was added a solution of K2CO3 (252 mg, 1.8 mmol) in H2O (3 mL) and the mixture was stirred until a homogeneous solution was obtained. Bicyclo[2.2.2]oct-5-en-2,3-dicarboxylic anhydride (452 mg, 2.5 mmol) was added and the mixture was heated to reflux temperature and allowed to react for 19 hrs. After cooling to room temperature, the reaction mixture was washed with EtOAc and acidified with conc. HCl until the pH reached 1. The aqueous phase was extracted with EtOAc and the organic phase washed with 5% HCl followed by brine and then dried over Na2SO4. Removal of the solvent gave a colorless solid which was recrystallized from EtOAc/hexane to yield the pure product as colorless crystals: 475 mg (58% yield), mp=161° C.

Workup

  1. customwas obtained
  2. temperaturethe mixture was heated
  3. temperatureto reflux temperature
  4. customto react for 19 hrs
  5. washthe reaction mixture was washed with EtOAc
  6. extractionThe aqueous phase was extracted with EtOAc
  7. washthe organic phase washed with 5% HCl
  8. dry with materialdried over Na2SO4
  9. customRemoval of the solvent
  10. customgave a colorless solid which
  11. customwas recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-e794eaa82a9a4be3ade8985f27224a00
Source dataset
uspto-grants-2000_08
Patent number
US06096811

Reaction notes

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