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Preparation method of sodium phenylbutyrate

A technology of sodium phenylbutyrate and preparation, applied in the field of preparation of sodium phenylbutyrate, can solve the problems of low product yield, complicated post-processing purification process, many synthesis steps, etc. The effect of high regioselectivity and yield, and excessive resolution steps

Active Publication Date: 2019-10-11
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, in the existing synthetic method of sodium phenylbutyrate, there are generally many synthetic steps, poor reaction regioselectivity, low product yield, and the reaction conditions are not mild, and the reaction and post-treatment purification process are relatively complicated.

Method used

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  • Preparation method of sodium phenylbutyrate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] (1) Under an argon atmosphere, add the material and anhydrous 2,3-butanediol in a molar volume ratio of 0.1mmol:0.1mL to the reaction vessel and mix well; wherein, the related materials include a molar ratio of 1: 3:0.01:0.2:5:3:100 of N-(octaaminoquinoline)but-3-enamide, bromobenzene, allylpalladium(II) chloride dimer, 2-(dicyclohexylphosphine Acyl)-1-phenyl-1H-pyrrole, lithium acetate, cyanoacetic acid and water;

[0019] (2) Place the reaction vessel in an oil bath at 125°C and vigorously stir for 12 hours, and purify the reaction product through a silica gel column (flush the chromatography silica gel column with petroleum ether at a ratio of 1:20 to ethyl acetate), to obtain The compound is determined to be 4-phenyl-N-(quinolin-8-yl)butanamide through detection.

Embodiment 2

[0021] This embodiment is basically the same as Embodiment 1, the difference is:

[0022] In step (1), N-(octaaminoquinoline)but-3-enamide, bromobenzene, allylpalladium(II) chloride dimer, 2-(dicyclohexylphosphono)-1- The molar ratio of phenyl-1H-pyrrole, lithium acetate, cyanoacetic acid and water is 1:1:0.1:0.02:1:1:1;

[0023] In step (2), the temperature of the oil bath is 130°C.

Embodiment 3

[0025] This embodiment is basically the same as Embodiment 1, the difference is:

[0026] In step (1), N-(octaaminoquinoline)but-3-enamide, bromobenzene, allylpalladium(II) chloride dimer, 2-(dicyclohexylphosphono)-1- The molar ratio of phenyl-1H-pyrrole, lithium acetate, cyanoacetic acid and water is 1:2:0.05:0.1:3:2:50;

[0027] In step (2), the temperature of the oil bath is 135°C.

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Abstract

The invention discloses a preparation method of sodium phenylbutyrate. The preparation method comprises the steps that in the inert atmosphere, materials and anhydrous 2,3-butanediol are added into areaction vessel, and mixing is conducted uniformly, wherein the related materials include allyl palladium (II) chloride dimer, 2-(dicyclohexylphosphino)-1-phenyl-1H-pyrrole, N-(8-aminoquinoline)butyl-3-enamide, lithium acetate, bromobenzene, cyanoacetic acid and water; the reaction vessel is placed in an oil bath at 125-135 DEG, a vigorous stirring reaction is conducted for 12 hours, a reaction product is purified through a silica gel column, and a compound with a guiding group is obtained; the compound is added into an ethanol solvent containing sodium hydroxide, the mixture is heated to 130-140 DEG C, a reflux reaction is conducted for 12 hours, the reaction product is subjected to vacuum distillation to remove the solvent, extraction is conducted, a water layer is collected, vacuum distillation is conducted to remove water, and a sodium phenylbutyrate preparation is obtained. The method has the advantages of being high in reaction site selectivity and yield, mild in reaction condition and simple in reaction and aftertreatment purification process.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, in particular to a preparation method of sodium phenylbutyrate. Background technique [0002] Sodium phenylbutyrate is a prodrug that is rapidly metabolized to phenylacetate. It can be combined with glutamic acid and ammonia to form phenylacetylglutamine, which is excreted through the kidneys, which is another way for nitrogenous waste to be excreted. Taking sodium phenylbutyrate can reduce the high blood ammonia level and blood glutamic acid concentration, and increase the excretion of nitrogenous waste in the form of phenylacetyl glutamine. It is suitable for all neonatal enzyme deficiency (complete enzyme deficiency within 28 days after birth), delayed enzyme deficiency (partial enzyme deficiency after the first month of life) with a family history of hyperammonemic encephalopathy . [0003] However, in the existing synthetic method of sodium phenylbutyrate, there are generally ma...

Claims

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Application Information

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IPC IPC(8): C07C51/41C07C57/30
CPCC07C51/41C07D215/40C07C57/30
Inventor 吴晓进郑可旺
Owner NANJING UNIV OF TECH
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