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Method for preparing sulindac

A technology of sulindac and indene acetic acid is applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., and can solve problems such as cumbersome operations

Active Publication Date: 2019-07-19
HANGZHOU LUPU BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Because the E-type isomer of 5-fluoro-2-methyl-1-(4-methylthiobenzylidene)-3-indene acetic acid can be partially converted into the Z-type isomer under certain conditions, in the actual process , in order to increase the yield of sulindac, it is usually necessary to carry out multiple recrystallizations and reaction conversions of 5-fluoro-2-methyl-1-(4-methylthiobenzylidene)-3-indene acetic acid, which is cumbersome to operate

Method used

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  • Method for preparing sulindac
  • Method for preparing sulindac
  • Method for preparing sulindac

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preparation example Construction

[0022] The invention provides a kind of preparation method of sulindac, comprising the following steps:

[0023] Mix 5-fluoro-2-methyl-1-(4-methylthiobenzylidene)-3-indene acetic acid, photosensitizer, oxidizing agent and reaction solvent, and carry out oxidation reaction under ultraviolet light irradiation conditions to obtain sulindac acid;

[0024] Wherein, the 5-fluoro-2-methyl-1-(4-methylthiobenzylidene)-3-indene acetic acid includes E-type isomer and Z-type isomer.

[0025] The preparation method of sulindac provided by the invention directly uses 5-fluoro-2-methyl-1-(4-methylthiobenzylidene)-3- Indene acetic acid is obtained as a raw material through an oxidation reaction to obtain sulindac without the need for repeated recrystallization and The reaction is transformed and the operation is simple. In the present invention, the proportion of the Z-type isomer in the 5-fluoro-2-methyl-1-(4-methylthiobenzylidene)-3-indeneacetic acid is preferably 50-92%. The present in...

Embodiment 1

[0041] Add 25g of 5-fluoro-2-methyl-1-(4-methylthiobenzylidene)-3-indene to a 1L reaction vessel equipped with a thermometer, a stirrer and a UV light source (wavelength range 315-400nm) Acetic acid (Z:E=66:33), 5.6g peroxyacetic acid, 0.5g anthracene and 300g ethanol were reacted at 25°C and 300r / min for 5h under the condition of ultraviolet light irradiation; after the reaction was completed, evaporated from the obtained system 250g of ethanol was cooled to 10°C for recrystallization, and suction filtered to obtain 25.5g of sulindac with a yield of 97.4% and a purity greater than 99.5%.

[0042] figure 1 For the proton nuclear magnetic spectrum of the product prepared in this embodiment, the data are as follows:

[0043] 1 HNMR (500MHz, CDCl 3 )δ7.71(d, J=8.2Hz, 2H), 7.63(d, J=8.2Hz, 2H), 7.14(s, 1H), 7.11(dd, J=8.4, 5.1Hz, 1H), 6.88( dd,J=8.8,2.3Hz,1H),6.54(td,J=8.9,2.3Hz,1H),3.58(s,2H),2.83(s,3H),2.20(s,3H).

[0044] Depend on figure 1 It can be seen from the above d...

Embodiment 2

[0046] Add 25g of 5-fluoro-2-methyl-1-(4-methylthiobenzylidene)-3-indene to a 1L reaction vessel equipped with a thermometer, a stirrer and a UV light source (wavelength range 315-400nm) Acetic acid (Z:E=66:33), 6.15g peroxyacetic acid, 0.5g anthracene and 375g toluene were reacted at 10°C and 300r / min for 12h under the condition of ultraviolet light irradiation; after the reaction was completed, the obtained system was evaporated to dryness, The residue was dissolved in 50 g of ethanol, cooled to 10°C for recrystallization, and suction filtered to obtain 25.9 g of sulindac with a yield of 98.9% and a purity greater than 99.0%.

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Abstract

The invention relates to the technical field of medicine composition and in particular relates to a method for preparing sulindac. The method comprises the following steps: mixing 5-fluorine-2-methyl-1-(4-methyl thiobenzene methylene)-3-indene acetic acid, a photosensitizer, an oxidant and a reaction solvent, and carrying out an oxidation reaction under an ultraviolet radiation condition, therebyobtaining sulindac, wherein the 5-fluorine-2-methyl-1-(4-methyl thiobenzene methylene)-3-indene acetic acid comprises an E-shaped isomer and a Z-shaped isomer. By adopting the method provided by the invention, the sulindac is prepared from the 5-fluorine-2-methyl-1-(4-methyl thiobenzene methylene)-3-indene acetic acid of the E-shaped isomer and the Z-shaped isomer as raw materials through the oxidation reaction directly, separation purification is avoided, and the operation is simple. Experiment results of the embodiment show that when the sulindac is prepared by using the method provided by the invention, the yield is up to 98.9%, the purity is greater than 99.5%, and the method has the advantages of being high in yield and good in purity.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a preparation method of sulindac. Background technique [0002] Sulindac is a non-steroidal anti-inflammatory drug mainly used to treat pain, rheumatoid arthritis, low back pain spondylitis and gouty arthritis. This drug is also used to treat premature labor and diabetic senile cataract. In recent years, the application of sulindac in tumor treatment has attracted the attention of researchers. Many studies have shown that sulindac has the ability to inhibit the growth of tumor cells, so the research on this type of product has aroused the attention of the world's scientific and public opinion circles. extensive attention. [0003] In the synthetic method of sulindac reported in existing documents and patents, 5-fluoro-2-methyl-1 -(4-methylthiobenzylidene)-3-indene acetic acid, the main configuration of the obtained 5-fluoro-2-methyl-1-(4-methylthiobenzylidene)-3-indene a...

Claims

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Application Information

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IPC IPC(8): C07C315/02C07C317/44
CPCC07C315/02C07C2602/08C07C317/44
Inventor 徐伟明冯冬祥李万梅章鹏飞陶连芝沈鸿云
Owner HANGZHOU LUPU BIOTECH CO LTD
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