(4R)-4-methyl-2-carbonyl valerate compound, synthesizing method and application

A technology of carbonyl valerate and synthesis method, which is applied in chemical instruments and methods, preparation of organic compounds, preparation of carboxylate, etc., can solve problems such as single structure, and achieve the effect of single structure and stable compound

Inactive Publication Date: 2011-04-13
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The mother liquor concentrate contains organic impurities and inorganic salts. The problem to be sol

Method used

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  • (4R)-4-methyl-2-carbonyl valerate compound, synthesizing method and application
  • (4R)-4-methyl-2-carbonyl valerate compound, synthesizing method and application
  • (4R)-4-methyl-2-carbonyl valerate compound, synthesizing method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The synthesis of embodiment 1 compound 3

[0029]

[0030] Take 2500g of crude compound (containing 20-30% of compound 2, if it contains more water, add toluene to reflux and divide the water to remove most of the water), under mechanical stirring, add anhydrous methanol to completely dissolve it, and slowly add concentrated hydrochloric acid Acidify to acidic pH=2, remove the white solid by suction filtration, spin dry the filtrate, add an appropriate amount of ethyl acetate to dissolve, dry with anhydrous sodium sulfate, filter, and spin off the solvent under reduced pressure to obtain 190 g of black oily liquid compound 3. The weight yield was 38%.

Embodiment 2

[0031] The synthesis of embodiment 2 compound 4a

[0032]

[0033] Take 100g of compound 3, add 500ml of toluene and 81g (3eq) of ground sodium hydroxide, reflux and divide water for 3 hours to remove the water absorbed during the grinding process of sodium hydroxide, slowly add 128ml (1.6eq) of benzyl bromide in portions ), reflux and divide water for 7 hours, add water after cooling to completely dissolve the system, extract twice with ether to remove impurities, add concentrated sulfuric acid to acidify to pH=1 under mechanical stirring, extract three times with ethyl acetate, combine the organic phases with saturated salt Wash once with water, dry with anhydrous sodium sulfate, filter, spin off the solvent under reduced pressure, dissolve in 600ml of anhydrous methanol, add 5ml (0.13eq) of concentrated sulfuric acid, stir at room temperature for 11 hours, dilute with water, spin off the methanol under reduced pressure, the water phase Extracted 3 times with ethyl acetat...

Embodiment 3

[0035] The synthesis of embodiment 3 compound 4b

[0036]

[0037]Take 100g of compound 3, add 500ml of toluene and 151g (4eq) of ground potassium hydroxide, reflux and divide water for 4 hours to remove the water absorbed during the grinding process of sodium hydroxide, slowly add 274ml of p-methoxybenzyl chloride (3eq), react at 80°C for 10 hours, add water after cooling to completely dissolve the system, extract twice with ether to remove impurities, add concentrated sulfuric acid to acidify to pH=2 under mechanical stirring, extract three times with ethyl acetate, and combine the organic phases Wash once with saturated brine, dry over anhydrous sodium sulfate, filter, spin off the solvent under reduced pressure, dissolve in 600ml of anhydrous methanol, add 3.6ml of concentrated sulfuric acid (0.1eq), stir at room temperature for 10 hours, dilute with water, spin off under reduced pressure Methanol, the aqueous phase was extracted 3 times with ethyl acetate, the organic ...

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Abstract

The invention relates to a (4R)-4-methyl-2-carbonyl valerate compound with a methyl chiral functional group. The compound is prepared by converting waste (2R,4R)-2,5-dyhydroxyl-4-methyl potassium valerate which is oxidatively degraded by steroidsapogenin. The method is easy and convenient to operate, not only can improve the utilization rate of the steroidsapogenin, but also reduces pollution of waste of sterides degradation to the environment.

Description

technical field [0001] The invention relates to a class of (4R)-4-methyl-2-oxovalerate compounds with methyl chiral functional groups and a preparation method thereof. They are obtained by solvent extraction and chemical transformation from steroidal saponin oxidative degradation waste containing (2R,4R)-2,5-dihydroxy-4-methylvalerate. The prepared raw materials are easy to obtain, and the operation method is simple and convenient. technical background [0002] A chiral synthetic reagent with a bifunctional structural feature of a chiral methyl side chain is widely used in organic synthesis. They have further extended bifunctional groups, and other chiral synthons can be obtained relatively easily. Due to their importance in the synthesis of bioactive substances and functional materials and their wide application, their preparation methods have received special attention. [0003] Bifunctional chiral synthetic reagents with chiral methyl side chains can be prepared by asym...

Claims

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Application Information

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IPC IPC(8): C07C69/738C07C205/34C07C67/313C07C201/12C07C47/277C07C45/40
Inventor 田伟生张顺吉汪昀
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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