L-Tyrosine → HCID 53969749, compound

HRID 1761361Notes

Reaction equation

HRID 1761361 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.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:26](O)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]>C1(C)C=CC=CC=1.O>[CH2:39]([O:12][C:11](=[O:13])[C@H:2]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)[NH2:1])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH3:26]

Participants

6

Reactant 3

HCID 6057L-TyrosineHCID 82091-TetradecanolHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 53969749HCID 53969749, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent3×

Procedure

9.1 g (0.05 mole) of L-tyrosine was used, 11.4 g (0.06 mole) of p-toluenesulfonic acid hydrate was used, and 11.79 g (0.055 mole) of myristyl alcohol was used as an alcohol. After 200 ml of toluene was added thereto as a solvent, these materials were stirred and mixed well. The resulting reaction mixture was heated at the reflux temperature of toluene to carry out the esterification reaction. In this case, water was formed with the progress of the esterification reaction and released in the form of an azeotropic mixture with toluene, which was continuously removed from the reaction system. Thus, the reaction was completed in about 7-15 hours. After being cooled to room temperature, the reaction mixture was poured into a separating funnel and treated with 200 ml of a mixture of 0.2N NaOH and 3M NaCl solutions. This treatment was repeated three times. Thereafter, the toluene layer was isolated and washed thoroughly with water. After washing with water, the toluene layer was isolated and dried overnight over anhydrous sodium sulfate. After drying, the toluene layer was filtered and the resulting toluene solution was evaporated to remove the solvent. Thus, there was obtained 15.1 g (80% yield) of purified free L-tyrosine myristyl ester in the form of an oily material.

Workup

  1. additionmixed well
  2. customThe resulting reaction mixture
  3. customthe esterification reaction
  4. customwas continuously removed from the reaction system
  5. additionthe reaction mixture was poured into a separating funnel
  6. additiontreated with 200 ml of a mixture of 0.2N NaOH and 3M NaCl solutions
  7. customThereafter, the toluene layer was isolated
  8. washwashed thoroughly with water
  9. washAfter washing with water
  10. customthe toluene layer was isolated
  11. dry with materialdried overnight over anhydrous sodium sulfate
  12. customAfter drying
  13. filtrationthe toluene layer was filtered
  14. customthe resulting toluene solution was evaporated
  15. customto remove the solvent

Sources & evidence

ORD record
ord-2d0f171498044037b6651a02d44d12cb
Source dataset
uspto-grants-1989_05
Patent number
US04826818

Reaction notes

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