L-Alanine → HCID 86742964, compound

HRID 1761355Notes

Reaction equation

HRID 1761355 reaction equation
[NH2:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].O.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14]([OH:17])(=[O:16])=[O:15])=[CH:10][CH:9]=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>[C:8]1([CH3:18])[CH:9]=[CH:10][C:11]([S:14]([OH:17])(=[O:15])=[O:16])=[CH:12][CH:13]=1.[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 86742964HCID 86742964, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent3×HCID 962WaterSolvent

Procedure

4.46 g (0.05 mole) of L-alanine 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 benzene was added thereto as a solvent, these materials were stirred and mixed well. The resulting 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. Then, the reaction mixture was concentrated under reduced pressure to remove the benzene used as solvent. After the addition of ether and petroleum ether, the precipitated crystals were collected by filtration. These crude crystals were recrystallized from acetone, ether, petroleum ether and the like to obtain 21.74 g (95% yield) of L-alanine myristyl ester p-toluenesulfonate. An infrared absorption spectrum of the L-alanine myristyl ester p-toluenesulfonate thus obtained is shown in FIG. 3. In this figure, the peak 5 indicates the absorption of light by a parasubstituted phenyl group, the peaks 6 and 7 by the ester linkage, the peak 8 by sulfonic acid, the peaks 9 and 10 by a primary amine salt, and the peak 11 by the C=O stretching vibration originating from the ester linkage.

Workup

  1. additionmixed well
  2. customthe esterification reaction
  3. customwas continuously removed from the reaction system
  4. concentrationThen, the reaction mixture was concentrated under reduced pressure
  5. customto remove the benzene
  6. additionAfter the addition of ether and petroleum ether
  7. filtrationthe precipitated crystals were collected by filtration
  8. customThese crude crystals were recrystallized from acetone, ether, petroleum ether

Sources & evidence

ORD record
ord-4ac3042f65e04ce19ef766a5507b1445
Source dataset
uspto-grants-1989_05
Patent number
US04826818

Reaction notes

Loading…