L-Phenylalanine → HCID 39100030, compound

HRID 895505Notes

Reaction equation

HRID 895505 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-])=O.[NH2:11][C@H:12]([C:20](O)=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)(O)[O-].[Na+]>C(O)C.O>[CH2:13]([C@@H:12]1[NH:11][C:2]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[NH:8][C:20]1=[O:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 6140L-PhenylalanineHCID 738951-Fluoro-2-nitrobenzeneHCID 516892Sodium Bicarbonate

Product 1

HCID 39100030HCID 39100030, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To ortho-fluoronitrobenzene (18) (6.5 g, 46 mmol) in ethanol (200 mL) and water (200 mL) under nitrogen was added L-phenylalanine (5.10 g, 31 mmol) and sodium bicarbonate (5.19 g, 62 mmol) and the suspension heated at reflux for 48 h. The red solution was coled, extracted with ether (2×50 mL—to remove any unreacted ortho-fluoronitrobenzene and concentrated to ½ volume. Pd/C (20%, 0.5 g) was added and a hydrogen balloon was attached. After stirring overnight the mixture was filtered, acidifed with 1N HCl to pH 4 and the solid that formed was collected. This was dried under high vacuum to afford the title compound (4.66 g, 53%) of sufficient purity (19) to use directly.

Workup

  1. temperaturethe suspension heated
  2. temperatureat reflux for 48 h
  3. extractionextracted with ether (2×50 mL—
  4. customto remove any unreacted ortho-fluoronitrobenzene
  5. concentrationconcentrated
  6. additionPd/C (20%, 0.5 g) was added
  7. filtrationwas filtered
  8. customthe solid that formed
  9. customwas collected
  10. customThis was dried under high vacuum

Sources & evidence

ORD record
ord-268a81b0432440598dc101a717c6148e
Source dataset
uspto-grants-2005_07
Patent number
US06916805B2

Reaction notes

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