L-Valine methyl ester hydrochloride

Chemical properties

Crystalline

The Uses of L-Valine methyl ester hydrochloride

L-Valine Methyl Ester Hydrochloride is used in the synthesis of Valaciclovir (V085000), the L-Valine ester prodrug of Acyclovir (A192400), orally active acyclic nucleoside with inhibitory activity tow ards several herpes viruses. Antiviral.

The Uses of L-Valine methyl ester hydrochloride

L-Valine Methyl Ester Hydrochloride is used in the synthesis of Valaciclovir (V085000), the L-Valine ester prodrug of Acyclovir (A192400), orally active acyclic nucleoside with inhibitory activity towards several herpes viruses. Antiviral.

Description

L-Valine methyl ester hydrochloride may serve as a convenient and available synthon for synthesising chiral nitrogen-containing organic compounds. The condensation of L-valine methyl ester hydrochloride with substituted benzaldehydes in the presence of sodium hydrogen carbonate (at the ratio of the stoichiometric reagents 1:1:1) afforded new chiral alkyl aromatic azomethines (Schiff bases) containing ether and ester groups.

Preperation

A preparation method of L-valine methyl ester hydrochloride which comprises the following steps: firstly, adding absolute methanol in a reactor and controlling the temperature between 8 ℃ below zero and 10 ℃ below zero, dripping thionyl phthalyl chloride by stirring, reacting for 0.8-1.5 hours at the temperature, adding L-valine under the cooling condition, raising the temperature to the ambient temperature and stirring for 2.5-3.5 hours, then heating and refluxing, and reacting for 7-9 hours at the temperature of 60-70 DEG C; and secondly, reducing pressure to distil after the reaction, cooling residues for crystallization, carrying out vacuum filtration, and recrystallizing with absolute methyl-ethyl ether to prepare L-valine methyl ester hydrochloride, wherein the reaction materials have the mole ratio that n (L-valine):n (SOC12):n (absolute methanol)=1.0:1-1.5:20-21。