A NEW PREPARATION METHOD OF 1-[1'-(CARBOXYMETHYL)CYCLOPROPANE METHYLDISULFANYLMETHYL]CYCLOPROPANEACETIC ACID AND IT'S DERIVATIVES

• Main Authors: JI, KO WOON, SON, HYO BIN, HEOR, JUNG HEE, CHO, YANG RAI, YU, HYE RI, HAN,RA, PARK, JEONG BAE, JEONG, SEON YI
• Format: Patent
• Language: English; Korean
• Published: 18.07.2013
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; APPARATUS THEREFOR; CHEMISTRY; GENERAL METHODS OF ORGANIC CHEMISTRY; METALLURGY; ORGANIC CHEMISTRY

PURPOSE: A manufacturing method is provided to produce 1'- (carboxymethyl) cyclopropane methylbenzalde methyl cyclopropane acetic acid and its derivatives, the precursor of 1- (mercaptomethyl) cyclopropane acetic acid, which play significant role in synthesizing an anti-asthmatic drug 'montelukast'. CONSTITUTION: In a manufacturing method of 1' - (carboxymethyl) cyclopropane methylbenzalde methyl cyclopropane acetic acid (1), cyclopropane acetic acid derivatives (2, 3) of the structural formula are reacted with disodium disulfide (Na2S2) to produce disulfide compound of the structural formula and to hydrolyze disulfide compound with disodium disulfide (Na2S2). X in the formula is a halogen atom or a sulfonate group and Y is an organic acid derivative. And Y is alkyl ester or aryl ester easy to be hydrolyzed as inorganic base like caustic soda, sodium carbonate, potassium hydroxide, potassium carbonate. A solvent used in a substitution reaction of the disodium disulfide is polar organic solvent like dimethylformamide, dimethyl sulphoxide, tetrahydrofuran, the dioxane etc., alcohols like ethanol and methanol, nitriles like acetonitrile, acetone like ketones or mixed solvent of these organic solvents and water condylar mixed solvents. [Reference numerals] (AA) Hydrolysis