L-Tyrosine → HCID 66739249, compound

HRID 908069Notes

Reaction equation

HRID 908069 reaction equation
[NH2:1][C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.C([O:17][CH2:18][CH3:19])(=O)C>S(=O)(=O)(O)O.O.C(O)CCCCCCC.C1(C)C=CC=CC=1>[C:18]([O:10][C:7]1[CH:6]=[CH:5][C:4]([CH2:3][C@@H:2]([C:11]([OH:13])=[O:12])[NH2:1])=[CH:9][CH:8]=1)(=[O:17])[CH2:19][CH2:11][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 2

HCID 6057L-TyrosineHCID 8857Ethyl Acetate

Product 1

HCID 66739249HCID 66739249, compound

Reagents, catalysts & solvents 4

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

Procedure

9.06 g of tyrosine was dissolved in a solution of 10 g of concentrated sulfuric acid, 20 mL water, 10 mL of octanol, and 200 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 to provide an emulsion. About 150 mL of ethyl acetate was added to the emulsion to provide two phases. The aqueous phase was discarded and the organic phase washed with saturated Brine and dried over anhydrous sodium sulfate. The solvent was the removed under reduced pressure to provide tyrosine 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. customto provide an emulsion
  6. customto provide two phases
  7. washthe organic phase washed with saturated Brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customremoved under reduced pressure

Sources & evidence

ORD record
ord-d7d1a7278f3f47b38428a75fe3dc3c9a
Source dataset
uspto-grants-2011_09
Patent number
US08017159B2

Reaction notes

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