METHOD OF SYNTHESIS OF PROPARGYL AMMONIUM CHLORIDE DERIVATIVES

摘要

FIELD: organic chemistry and technology. SUBSTANCE: invention relates to a method of synthesis of L-isomers of derivatives of propargyl ammonium chloride of the general formula (I): <EMI ID=0.217 HE=18 WI=66 TI=CHI> where Y - hydrogen or fluorine atom. Method involves decomposition of D-tartrate-L-isomer of amine of the general formula (II): <EMI ID=0.218 HE=18 WI=48 TI=CHI> where Y is indicated above and an interaction of obtained L-isomer of amine of the general formula (II) in the presence of the base with halogenide of the general formula (V): X-<EMI ID=0.219 HE=6 WI=15 TI=CHI> where X - halogen atom followed by interaction of obtained L-isomer of the general formula (III): <EMI ID=0.220 HE=15 WI=69 TI=CHI> with hydrogen chloride in an organic solvent. During this reaction amine base is released from D-tartrate-L-isomer of amine of the general formula (II) in an aqueous suspension using ammonium hydroxide or alkaline metal salt and/or ammonium salt and its interaction with 1-1.5 mole equivalent of halogenide of the general formula (V) at 0-50 C in buffer system, pH = 8-12. After separation of an aqueous layer a mixture containing L-isomers of amines of the general formula (II) and (III) in an organic solvent is extracted with water and a mixture of ammonium hydroxide and water and/or with phosphate salt an aqueous solution, pH = 5.5-7.5. Then L-isomer of amine of the general formula (II) or its salts is dissolved in an aqueous layer and separated its from L-isomer of amine of the general formula (III) and converted then to L-isomer of amine of the general formula (III) after distillation to L-isomer of salt of the general formula (I). EFFECT: production of pure racemic forms of product. 2 cl, 13 ex