L-Alanine → HCID 86742964, compound

Participants

Reaction Steps

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.

Provenance & Evidence