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Method for synthesizing (S)-2-hydroxy-2'-(3-phenylureaphenyl)-1,1'-binaphthyl-3-formaldehyde

A technology of phenylureabenzyl and phenylureidobenzyloxy is applied in the field of synthesizing -2-hydroxy-2'--1,1'-binaphthyl-3-formaldehyde, and can solve the problem of being unsuitable for industrialized large-scale production , poor regioselectivity, complex operation, etc., to avoid the formation of complex by-products, easy to obtain, and good reaction selectivity

Inactive Publication Date: 2011-05-25
BOHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The regioselectivity of the reaction in method 1 is not good, and the yield is also very low
The preparation process of the intermediate 2'-methoxymethyl-3-formyl-binaphthalene in method 2 is complicated to operate, difficult to control, and the yield is not good, so it is not suitable for large-scale industrial production

Method used

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  • Method for synthesizing (S)-2-hydroxy-2'-(3-phenylureaphenyl)-1,1'-binaphthyl-3-formaldehyde
  • Method for synthesizing (S)-2-hydroxy-2'-(3-phenylureaphenyl)-1,1'-binaphthyl-3-formaldehyde
  • Method for synthesizing (S)-2-hydroxy-2'-(3-phenylureaphenyl)-1,1'-binaphthyl-3-formaldehyde

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Experimental program
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Effect test

Embodiment 1

[0017] Take 3-formyl-1,1'-binaphthol (2) as raw material, dissolve it in a certain amount of methanol, cool in an ice bath to 10°C, add sodium borohydride, 3-formyl-1,1'- The molar ratio of binaphthol to sodium borohydride is 1.0:1.0, and the reduction reaction is carried out at room temperature to obtain 3-hydroxymethyl-1,1'-binaphthol (3); sulfuric acid) condition, the molar ratio of concentrated sulfuric acid to 3-hydroxymethyl-1,1'-binaphthol (3) is 0.01:1, add 2,2'-dimethoxypropane, 3- The molar ratio of hydroxymethyl-1,1'-binaphthol (3) to 2,2'-dimethoxypropane is 1.0:2.0. After the reaction at room temperature, it is extracted with an organic solvent (ethyl acetate), concentrated , separated by column chromatography to obtain the product ( S )-2-hydroxyl-1-(2,2,-dimethyl-1,3-dioxo-1,2,3,4-tetrahydroanthracene-9-)-naphthalene (4), yield 85 %; Then use dry DMF as solvent, add sodium hydride under ice-cooling, add 3-(4-methoxyphenyl)-ureido-benzyl bromide after one hour ...

Embodiment 2

[0019] Take 3-formyl-1,1'-binaphthol (2) as raw material, dissolve it in methanol, cool in an ice bath to 5°C, add sodium borohydride, 3-formyl-1,1'-bis The molar ratio of naphthol to sodium borohydride is 1.0:1.5, and the reduction reaction is carried out at room temperature to obtain 3-hydroxymethyl-1,1'-binaphthol (3); then use acetone as a solvent in the catalyst (concentrated sulfuric acid ) conditions, the molar ratio of concentrated sulfuric acid to 3-hydroxymethyl-1,1'-binaphthol (3) is 0.05:1, adding 2,2'-dimethoxypropane, 3-hydroxymethyl The molar ratio of base-1,1'-binaphthol (3) to 2,2'-dimethoxypropane is 1.0:3.0. After reaction at room temperature, it is extracted with organic solvent (ethyl acetate), concentrated, and column layer The product was obtained by analysis and separation ( S )-2-hydroxyl-1-(2,2,-dimethyl-1,3-dioxo-1,2,3,4-tetrahydroanthracene-9-)-naphthalene (4), yield 87 %; then use dry DMF as a solvent, add sodium hydride under ice-cooling, add 3-...

Embodiment 3

[0021]Take 3-formyl-1,1'-binaphthol (2) as the raw material, dissolve it in methanol, cool in an ice bath to 0°C, add sodium borohydride, 3-formyl-1,1'-bis The molar ratio of naphthol to sodium borohydride is 1.0:2.0, and the reduction reaction is carried out at room temperature to obtain 3-hydroxymethyl-1,1'-binaphthol (3); then use acetone as a solvent in the catalyst (concentrated sulfuric acid ) conditions, the molar ratio of concentrated sulfuric acid to 3-hydroxymethyl-1,1'-binaphthol (3) is 0.03:1, add 2,2'-dimethoxypropane, 3-hydroxymethyl-1 , the molar ratio of 1'-binaphthol (3) to 2,2'-dimethoxypropane is 1.0: 4.0, after reaction at room temperature, it is extracted with an organic solvent (ethyl acetate), concentrated, and separated by column chromatography to obtain product( S )-2-Hydroxy-1-(2,2,-dimethyl-1,3-dioxo-1,2,3,4-tetrahydroanthracene-9-)-naphthalene (4), yield 90 %; Then use dry DMF as solvent, add sodium hydride under ice-cooling, add 3-(4-methoxypheny...

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Abstract

The invention discloses a method for synthesizing (S)-2-hydroxy-2'-(3-phenylureaphenyl)-1,1'-binaphthyl-3-formaldehyde, which uses widely available raw materials, makes operation easy, has high yield and produces little pollution. The method comprises the following process steps: dissolving 3-formoxyl-1,1'-binaphthol serving as a raw material in methanol, cooling in an ice bath, adding sodium borohydride, and reducing to obtain 3-hydroxymethyl-1,1'-binaphthol; dissolving 3-hydroxymethyl-1,1'-binaphthol in acetone serving as a solvent, adding 2,2'-dimethoxypropane to perform a reaction in the presence of a catalyst, extracting with an organic solvent, and obtaining (S)-2-hydroxy-1-(2,2-dimethyl-1,3-dioxo-1,2,3,4-tetrahydroanthracene-9-)-naphthalene by column chromatograpic separation; dissolving (S)-2-hydroxy-1-(2,2-dimethyl-1,3-dioxo-1,2,3,4-tetrahydroanthracene-9-)-naphthalene in dry dimethyl formamide (DMF) serving as a solvent, adding sodium hydride under an ice bath condition, reacting for 0.5 and 1 hours, adding 3-(4-methoxyphenyl)-ureido-benzyl bromide, reacting and obtaining (S)-2-(3-phenylureidobenzoxy)-1-(2,2-dimethyl-1,3-dioxo-1,2,3,4-tetrahydroanthracene-9-)- naphthalene by column chromatograpic separation; dissolving the (S)-2-(3-phenylureidobenzoxy)-1-(2,2-dimethyl-1,3-dioxo-1,2,3,4-tetrahydroanthracene-9-)- naphthalene in glycol serving as a solvent, heating to remove a protective group under the action of p-toluenesulfonic acid and reacting to obtain (S)-2-hydroxy-3-hydroxymethyl-2'-(3-tetrahydroanthracene)-1,1'-binaphthyl; and finally, oxidizing the (S)-2-hydroxy-3-hydroxymethyl-2'-(3-tetrahydroanthracene)-1,1'-binaphthyl in dry dichloromethane by pyridinium chlorochromate, and after reaction, filtering the reaction product by kieselguhr, concentrating and performing column chromatograpic separation to obtain the target product.

Description

technical field [0001] The present invention relates to a kind of synthesis ( S )-2-hydroxy-2'-(3-phenylureabenzyl)-1,1'-binaphthyl-3-carbaldehyde. Background technique [0002] Recent studies have shown that some ureido-based binaphthol derivatives can be used as artificial mimetic enzymes of pyridoxal phosphate to enantiomerize 1,2-aminoalcohols through a reversible reaction with chiral aminoalcohols to form a Schiff base. Select recognition and extraction resolution, and perform configuration conversion of L-amino acids and extraction resolution of racemic amino acids. Generally, L-amino acids can be obtained by fermentation, while D-amino acids cannot be produced by fermentation. D-amino acid is a key intermediate of chiral drugs, chiral pesticides, and chiral food additives, and has broad application prospects in the fields of medicine, pesticides, and food. use( S )-2-Hydroxy-2'-(3-phenylureabenzyl)-1,1'-binaphthyl-3-carbaldehyde (1) can convert readily available L...

Claims

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Application Information

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IPC IPC(8): C07C275/32C07C273/18
CPCY02P20/55
Inventor 汤立军郭志龙钱建华魏恭繁
Owner BOHAI UNIV
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