Sodium Iodide → Benzyl N,N-dibenzyl-L-phenylalaninate

HRID 259826Notes

Reaction equation

HRID 259826 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+].[I-].[Na+].[CH2:21](Cl)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(OCC)(=O)C.O.CN(C)C(=O)C>[CH2:21]([O:11][C:10](=[O:12])[C@H:2]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[N:1]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 6140L-PhenylalanineHCID 7503Benzyl ChlorideHCID 11430Potassium Carbonate

Product 1

HCID 10928230Benzyl N,N-dibenzyl-L-phenylalaninateYield 207.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

L-Phenylalanine (50 g), pulverized potassium carbonate (167 34 g), and sodium iodide (22.68 g) were added to N,N-dimethylacetamide (500 ml) while stirring, and water (25 ml) was added thereto. After elevating the temperature to 60° C., benzyl chloride (118.78 g) was dropwise added. After the dropwise addition, the mixture was vigorously stirred at 60°-65° C. for 6 hours. After the reaction, the reaction mixture was cooled to 20°-30° C., and water (750 ml) and ethyl acetate (500 ml) were added thereto for extraction. The ethyl acetate layer was separated, washed with water (500 ml), an aqueous solution of 10% sodium hydrogensulfite (500 ml×2), and water (500 ml), and concentrated to dryness under reduced pressure to give N,N-dibenzyl-L-phenylalanine benzyl ester (136.88 g) as a yellow, oily substance.

Workup

  1. customto 60° C.
  2. additionAfter the dropwise addition
  3. stirringthe mixture was vigorously stirred at 60°-65° C. for 6 hours
  4. customAfter the reaction
  5. temperaturethe reaction mixture was cooled to 20°-30° C.
  6. extractionfor extraction
  7. customThe ethyl acetate layer was separated
  8. washwashed with water (500 ml)
  9. concentrationan aqueous solution of 10% sodium hydrogensulfite (500 ml×2), and water (500 ml), and concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-45aaf5d5d5d84248b95c8d57d27ddd7c
Source dataset
uspto-grants-1996_06
Patent number
US05523410

Reaction notes

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