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A kind of synthetic method of pharmaceutical intermediate benzyl ester compound

A synthesis method and compound technology, which are used in the synthesis of ester compounds and the synthesis field of benzyl ester compounds, can solve the problems of narrow reaction substrate range and low product yield, and achieve good application prospects and industrial production potential. Effect

Active Publication Date: 2018-07-10
内蒙古华洲药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are still some defects in these methods, such as low product yield, relatively narrow range of reaction substrates, etc.

Method used

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  • A kind of synthetic method of pharmaceutical intermediate benzyl ester compound
  • A kind of synthetic method of pharmaceutical intermediate benzyl ester compound
  • A kind of synthetic method of pharmaceutical intermediate benzyl ester compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038]

[0039] To an appropriate amount of organic solvent (an equal volume mixture of acetonitrile and polyethylene glycol 200 (PEG-200)) was added 100mmol of the compound of the above formula (I), 150mmol of the compound of the above formula (II), and 10mmol of the catalyst (2mmol(1,1) '-Bis(diphenylphosphine)ferrocene) nickel dichloride and 8mmol bis(triphenylphosphine) cuprous nitrate (Cu(PPh 3 ) 2 NO 3 )), 150mmol of oxidant 2-iodoylbenzoic acid (IBX) and 15mmol of accelerator tetraphenylporphyrin, then stirred and heated to 80°C, and stirred at this temperature for 10 hours.

[0040] After the reaction is over, filter the reaction solution while it is hot, adjust the pH value of the filtrate to neutral, and wash it with saturated brine and saturated sodium bicarbonate solution in sequence, then add acetone to fully shake and extract 2-3 times, combine the organic phases, Concentrated under reduced pressure, and the obtained residue was subjected to 300-400 mesh silica gel c...

Embodiment 2

[0043]

[0044] To an appropriate amount of organic solvent (an equal volume mixture of acetonitrile and polyethylene glycol 200 (PEG-200)) was added 100mmol of the above formula (I) compound, 200mmol of the above formula (II) compound, 15mmol catalyst (being 3mmol [1,1 '-Bis(diphenylphosphine)ferrocene]nickel dichloride and 12mmol bis(triphenylphosphine) cuprous nitrate (Cu(PPh 3 ) 2 NO 3 )), 200 mmol of the oxidizing agent 2-iodoyl benzoic acid (IBX) and 17 mmol of the accelerator tetraphenylporphyrin, then stirred and heated to 90°C, and stirred at this temperature for 9 hours.

[0045] After the reaction is over, filter the reaction solution while it is hot, adjust the pH value of the filtrate to neutral, and wash it with saturated brine and saturated sodium bicarbonate solution in sequence, then add acetone to fully shake and extract 2-3 times, combine the organic phases, Concentrated under reduced pressure, and the obtained residue was subjected to 300-400 mesh silica gel co...

Embodiment 3

[0048] The reaction formula is the same as in Example 1, and the specific operations are as follows:

[0049] Add 100mmol of the compound of formula (I), 250mmol of the compound of formula (II), 20mmol of catalyst (being 4mmol(1) to an appropriate amount of organic solvent (an equal volume mixture of acetonitrile and polyethylene glycol 200 (PEG-200)). ,1'-bis(diphenylphosphine)ferrocene]nickel dichloride and 16mmol bis(triphenylphosphine) cuprous nitrate (Cu(PPh 3 ) 2 NO 3 )), 250mmol of oxidant 2-iodoylbenzoic acid (IBX) and 20mmol of accelerator tetraphenylporphyrin, then stirred and heated to 100°C, and stirred at this temperature for 7 hours.

[0050] After the reaction is over, filter the reaction solution while it is hot, adjust the pH value of the filtrate to neutral, and wash it with saturated brine and saturated sodium bicarbonate solution in sequence, then add acetone to fully shake and extract 2-3 times, combine the organic phases, Concentrated under reduced pressure, a...

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Abstract

The present invention relates to a method for synthesizing benzyl ester compounds represented by the following formula (III) that can be used as pharmaceutical intermediates. The method includes: in an organic solvent, in the presence of a catalyst, an oxidizing agent and a promoter, The compound of formula (I) and the compound of formula (II) react, and after the reaction is completed, post-treatment is performed to obtain the compound of formula (III), wherein R1 is selected from H, C1-C6 alkyl, C1-C6 alkoxy Or halogen; R2 is selected from H, C1-C6 alkyl or halogen; R3 is selected from H or C1-C6 alkyl; X is halogen. The method can obtain the target product in high yield through the comprehensive selection and coordination of new composite catalysts, oxidants and accelerators, and organic solvents, and provides a new synthesis method for the synthesis of this type of compounds. It has great advantages in pharmaceutical intermediate synthesis technology. Good application prospects and industrial production potential.

Description

Technical field [0001] The invention relates to a method for synthesizing ester compounds, and more particularly to a method for synthesizing benzyl ester compounds that can be used as pharmaceutical intermediates, and belongs to the field of pharmaceutical intermediate synthesis. Background technique [0002] As we all know, benzyl ester structural units are used to construct a variety of biologically active molecules. At the same time, they are also used as key precursors in the construction and transformation of compounds, and thus play an important role in the synthesis of drugs and natural products. effect. In addition, benzyl ester groups are also important protecting groups in organic synthesis. [0003] Therefore, benzyl ester compounds have attracted more and more attention and attention. So far, great progress has been made in the synthesis of benzyl ester compounds. In recent years, relevant reports have emerged in endlessly, and gratifying achievements have been made...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/10C07C67/313C07C69/738B01J31/24
CPCC07C67/10C07C67/313B01J31/2404B01J35/19C07C69/738
Inventor 姜圆圆
Owner 内蒙古华洲药业有限公司