Method for preparing [1-(mercapto methyl) cyclopropyl] acetate and derivatives thereof

A technology of mercaptomethyl and cyanomethyl, which is applied in the field of preparing [1-cyclopropyl]acetic acid and its derivatives, can solve the problems of inconvenient industrial application, and achieve the effect of simple equipment and mild reaction conditions

Inactive Publication Date: 2008-06-18
FORMOSA LAB
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, it may contain disulfides of the final product, and it is very inconvenient for industrial applications at reaction temperatures below 0 °C

Method used

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  • Method for preparing [1-(mercapto methyl) cyclopropyl] acetate and derivatives thereof
  • Method for preparing [1-(mercapto methyl) cyclopropyl] acetate and derivatives thereof
  • Method for preparing [1-(mercapto methyl) cyclopropyl] acetate and derivatives thereof

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preparation example Construction

[0016] The invention provides a new method for preparing high-purity [1-(mercaptomethyl)cyclopropyl]acetic acid and its derivatives.

[0017] The present invention provides an efficient process with improved yield and purity for industrial applications.

[0018] Accordingly, the present invention provides a process for the preparation of [1-(mercaptomethyl)cyclopropyl]acetic acid of the formula,

[0019]

[0020] The above compounds are obtained by converting the compounds of the following formula with bases in alcoholic solvents,

[0021]

[0022] Wherein R represents an alkyl group and a cycloalkyl group, preferably a C1-10 alkyl group or a C3-10 cycloalkyl group, more preferably a C1-4 alkyl group, and most preferably a methyl group. This reaction is carried out at a temperature of about 30°C to about 99°C, preferably about 40°C to 90°C, more preferably about 50°C to 85°C, most preferably about 60°C to 80°C. The reaction is carried out for about 1-2 hours until the ...

Embodiment 1

[0062] Embodiment 1: Preparation [1-(bromomethyl) cyclopropyl] methyl acetate

[0063] 200 g of 1,1-cyclopropyldimethanol and 200 mL of dichloromethane were added to a 3 L three-necked round flask equipped with a mechanical stirrer, thermometer, nitrogen inlet and an additional funnel. The mixture was cooled to 0°C-5°C. Slowly add glacial acetic acid dissolved in 1440 g of 33% HBr into the reaction solution, and keep the temperature below 20°C. After the addition, the reaction mixture was stirred at 10°C to 18°C ​​for 2 hours, then the temperature of the reaction mixture was heated to between 16°C and 22°C and stirred for about 1 hour. After the raw material 1,1-cyclopropyldimethanol was completely dissolved (checked by TLC, mobile phase: EA / hx=1 / 3 (V / V)), 1000 mL of water was added to the reaction mixture, stirred for more than 30 minutes, And keep the temperature below 20°C. After the solution was separated into layers, the aqueous layer was back-extracted with 300 mL of ...

example 2

[0064] Example 2: Cyclopropane-1,1-diylbis(methylene)bisethyl ester

[0065] 2 g of 1,1-cyclopropyldimethanol, 5 g of acetic anhydride, 2 mL of dichloromethane, and 0.77 g of pyridine were added to a 50 mL three-neck round flask equipped with a condenser and a thermometer. The reaction mixture was heated to about 90°C-95°C and stirring was continued for about 1 hour. When the reaction was complete, the reaction mixture was cooled and 14.4 g of 33% hydrogen bromide in glacial acetic acid was added, keeping the temperature below 20°C. After the addition, the reaction mixture was stirred for about 6 hours, then 2 mL of dichloromethane and 10 mL of water were added. After the solution was separated into layers, the aqueous layer was extracted twice with 4 mL of dichloromethane. The organic layers were combined and washed twice with 6 mL of water, then the pH was adjusted to 8 with sodium carbonate solution. The organic layer was concentrated to obtain 3.3 g of crude methyl [1-(...

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Abstract

The invention relates to a preparation method of leukotriene antagonist, particularly the preparation method of 1-(sulfhydryl methyl)-cycloprophyl-acetate and the derivate thereof. The mentioned compound is prepared from the transformation of the compound in the below formula by the alkali of the alcohol solvent, wherein R represents the alkyl and the naphthenic radical.

Description

technical field [0001] The invention relates to a method for preparing a leukotriene antagonist, in particular to a method for preparing [1-(mercaptomethyl)cyclopropyl]acetic acid and its derivatives. Background technique [0002] The compound [1-(mercaptomethyl)cyclopropyl]acetic acid and its derivatives are an important intermediate in the synthesis of leukotriene receptor antagonists, wherein leukotriene receptor antagonists inhibit cysteine ​​leukotriene CysL T1 receptor. Leukotrienes are associated with inflammation and constriction of the tracheal muscles and accumulation of fluid in the lungs. A number of leukotriene antagonists have been disclosed in EP 480,717, EP 604,114 and US 5,270,324. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory and cytoprotective agents. They are also used to treat sore throat, cerebral spasms, glomerulonephritis, hepatitis, endotoxemia, uveitis, and rejection of allografts. [0003] The compounds disclose...

Claims

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Application Information

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IPC IPC(8): C07C323/53C07C319/12
Inventor 孙荣田刘育良魏庆鹏
Owner FORMOSA LAB
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