L-Alanine → HCID 54149372, compound

HRID 1761360Notes

Reaction equation

HRID 1761360 reaction equation
[NH2:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:19](O)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>C1C=CC=CC=1.O>[CH2:32]([O:5][C:4](=[O:6])[C@H:2]([CH3:3])[NH2:1])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH3:19]

Participants

6

Reactant 3

HCID 5950L-AlanineHCID 82091-TetradecanolHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 54149372HCID 54149372, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent3×HCID 962WaterSolvent

Procedure

4.46 g (0.05 mole) of L-alanine was taken, 11.4 g (0.06 mole) of p-toluenesulfonic acid hydrate was taken, and 11.79 g (0.055 mole) of myristyl alcohol was taken as an alcohol. After 200 ml of benzene was added thereto as a solvent, these materials were stirred and mixed well. The resulting reaction mixture was heated at the reflux temperature of benzene 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 benzene, 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 benzene layer was isolated and washed thoroughly with water. After washing with water, the benzene layer was isolated and dried overnight over anhydrous sodium sulfate. After drying, the benzene layer was filtered and the resulting benzene solution was evaporated to remove the solvent. Thus, there was obtained 13.7 g (96% yield) of purified free L-alanine 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 benzene layer was isolated
  8. washwashed thoroughly with water
  9. washAfter washing with water
  10. customthe benzene layer was isolated
  11. dry with materialdried overnight over anhydrous sodium sulfate
  12. customAfter drying
  13. filtrationthe benzene layer was filtered
  14. customthe resulting benzene solution was evaporated
  15. customto remove the solvent

Sources & evidence

ORD record
ord-6c680645ae9a4172b1477aac53399d61
Source dataset
uspto-grants-1989_05
Patent number
US04826818

Reaction notes

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