L-Phenylalanine → HCID 66739398, compound

HRID 2354538Notes

Reaction equation

HRID 2354538 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.[CH2:13](O)[CH2:14][CH2:15]CCCCCCCCC>S(=O)(=O)(O)O.O.C1(C)C=CC=CC=1>[C:10]([OH:12])(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:13][CH2:14][CH3:15].[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 2

HCID 6140L-PhenylalanineHCID 81931-Dodecanol

Product 1

HCID 66739398HCID 66739398, compound

Reagents, catalysts & solvents 3

HCID 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 dodecanol, 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 dodecanoate as a 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-9ec67028206e4b0288b888f9d6aa7bdc
Source dataset
uspto-grants-2010_07
Patent number
US07754679B2

Reaction notes

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