L-Phenylalanine → HCID 66739091, compound

HRID 908067Notes

Reaction equation

HRID 908067 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>S(=O)(=O)(O)O.O.C(O)CCCCCCC.C1(C)C=CC=CC=1>[C:10]([OH:12])(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[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

Participants

6

Reactant 1

HCID 6140L-Phenylalanine

Product 1

HCID 66739091HCID 66739091, compound

Reagents, catalysts & solvents 4

HCID 9571-OctanolSolventHCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolventHCID 1140TolueneSolvent

Procedure

16.52 g of phenylalanine was dissolved in a solution of 10 g of concentrated sulfuric acid, 20 mL water, 20 mL of octanol, and 120 mL of toluene in a 500 mL round bottom flask equipped with a condenser and a Dean-Stark apparatus. The resulting solution was heated at reflux temperature until no more water could be distilled. The resulting solution was then cooled to room temperature and washed with saturated aqueous sodium bicarbonate to neutralize acidic impurities, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was then removed under reduced pressure to provide phenylalanine octanoate as a white solid that was purified using a silica gel column eluted with a 1:9 methanol:dichloromethane mixture.

Workup

  1. customequipped with a condenser
  2. temperatureThe resulting solution was heated
  3. distillationcould be distilled
  4. washwashed with saturated aqueous sodium bicarbonate
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was then removed under reduced pressure

Sources & evidence

ORD record
ord-6f30c85ae81f4fe1ba11c29a5b5a30f9
Source dataset
uspto-grants-2011_09
Patent number
US08017159B2

Reaction notes

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