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Method for synthesizing N-(carbobenzoxy) succinimide by one-pot two-phase method

A technology of succinimide and benzyloxycarbonyl is applied in the field of one-pot two-phase synthesis of N-succinimide, which can solve the problems of high process cost, cumbersome synthesis steps, and high purity requirements of raw materials, so as to reduce the operation steps , The effect of reducing the process cost

Pending Publication Date: 2020-01-17
GENCHEM & GENPHARM CHANGZHOU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The technical problem to be solved by the present invention is: to overcome the technical problems of cumbersome synthesis steps of N-(benzyloxycarbonyl) succinimide in the prior art, high process cost, and high requirements for raw material purity, and to provide a one-pot two- The method for synthesizing N-(benzyloxycarbonyl)succinimide by phase method

Method used

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  • Method for synthesizing N-(carbobenzoxy) succinimide by one-pot two-phase method
  • Method for synthesizing N-(carbobenzoxy) succinimide by one-pot two-phase method
  • Method for synthesizing N-(carbobenzoxy) succinimide by one-pot two-phase method

Examples

Experimental program
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Effect test

Embodiment 1

[0025] In a 1000ml four-necked flask, add 100g of water, under stirring, add 125g of hydroxylamine sulfate (molecular weight 164.1, 0.76mol), dropwise add 200g of liquid caustic soda (molecular weight 40.0, 2mol) with a mass fraction of 40%, under stirring, drop into Diacid anhydride 152.3g (molecular weight 100.1, 1.52mol), all dissolved under stirring, add 5g of 85% phosphoric acid (molecular weight 98, 0.043mol), vacuum dehydration, control the temperature in the bottle is not higher than 160 ℃, until anhydrous comes out, cool down to Below 100°C, add 250g of toluene, heat up to reflux with stirring, reflux to separate water until no water comes out, and drop to 25-30°C. 500g of liquid caustic soda aqueous solution (mass fraction is 40% liquid caustic soda 100g, water 400g) is added dropwise in the reaction bottle, at this moment, the solid in the bottle disappears, and it is a two-phase distribution. With rapid stirring, 150g of benzyl chloroformate (molecular weight 170.6 ...

Embodiment 2

[0027] In a 1000ml four-neck flask, add 100g of water, under stirring, add 105g of hydroxylamine hydrochloride (molecular weight 164.1, 0.64mol), dropwise add 250g of liquid caustic soda (molecular weight 40.0, 2.5mol) with a mass fraction of 40%, and under stirring, drop in 152.3 g of succinic anhydride (molecular weight 100.1, 1.52 mol), stir to dissolve completely, add 5 g of sulfuric acid (molecular weight 98, 0.05 mol) with a mass fraction of 98%, vacuum dehydration, control the temperature in the bottle not higher than 160 ° C, until anhydrous Remove, lower the temperature to below 100°C, add 250g of toluene, raise the temperature to reflux with stirring, reflux to separate water until no water comes out, and drop to 25-30°C. Add 500 g of sodium carbonate aqueous solution (sodium carbonate 150 g, water 350 g) dropwise in the reaction bottle, at this moment, the solid in the bottle disappears, and it is a two-phase distribution. Quickly stir and dropwise add 130 g of benzy...

Embodiment 3

[0029] In a 1000ml four-necked flask, add 100g of water, under stirring, add 125g of hydroxylamine sulfate (molecular weight 164.1, 0.76mol), dropwise add 200g of liquid caustic soda (molecular weight 40.0, 2mol) with a mass fraction of 40%, and under stirring, drop into Diacid anhydride 145g (molecular weight 100.1, 1.45mol), stir to dissolve completely, add 85% phosphoric acid 5g (molecular weight 98, 0.043mol), vacuum dehydration, control the temperature in the bottle not higher than 160 ℃, until anhydrous, drop to 100 Below ℃, add 200g of toluene, raise the temperature to reflux under stirring, reflux to separate water until no water is separated, and drop to 25-30 ℃. Add 500 g of liquid caustic soda aqueous solution (mass fraction is 40% liquid caustic soda 100 g, water 300 g) dropwise in the reaction bottle, at this moment the solid in the bottle disappears, and it is a two-phase distribution, quickly stir and dropwise add 150 g of benzyl chloroformate with a molecular we...

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Abstract

The invention relates to the technical field of organic chemistry, in particularly to a method for synthesizing N-(carbobenzoxy) succinimide by one-pot two-phase method. The method comprises the following steps: adding purified water and hydroxylamine sulfate into a reaction container, dropwise adding liquid caustic soda while stirring, adding butanedioic anhydride in batches after dropwise addingis finished, and carrying out high-temperature vacuum dehydration under acid catalysis until no water is extracted so as to prepare an N-hydroxysuccinimide solution; adding an alkali into the N-hydroxysuccinimide solution to adjust the pH value of the reaction solution, controlling the temperature at 0-60 DEG C, and dropwise adding benzyl chloroformate; after dropwise adding, separating out an organic layer, concentrating to be dry, and recrystallizing to obtain an N-(carbobenzoxy) succinimide finished product. According to the method provided by the invention, separation and purifying stepsafter synthesis of the N-hydroxysuccinimide are avoided, and the N-(carbobenzoxy) succinimide is synthesized by directly adopting a two-phase method in a one-pot manner, so that the process cost is effectively reduced, the operation steps are reduced, and large-scale industrial production is facilitated.

Description

technical field [0001] The invention relates to the technical field of organic chemistry, in particular to a method for synthesizing N-(benzyloxycarbonyl)succinimide by a one-pot two-phase method. Background technique [0002] N-(Benzyloxycarbonyl)succinimide is a kind of efficient amino acid protecting agent, which is widely used in the synthesis of peptides. The synthetic route of N-(benzyloxycarbonyl)succinimide is mainly synthesized by the reaction of N-hydroxysuccinimide and benzyloxycarbonyl chloride. [0003] [0004] At present, the synthesis method of N-hydroxysuccinimide is relatively mature. The more commonly used method is the reaction of succinic anhydride and hydroxylamine (hydroxylamine is free from hydroxylamine hydrochloride or hydroxylamine sulfate). After a series of post-treatments, N-hydroxyl The finished product of succinimide. Such as Henan Chemical Industry, 1995 (5) 18; Applied Chemistry 2003.20 (6) 611; Jiangxi Chemical Industry 2002 (11) 37, e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/46
CPCC07D207/46
Inventor 王玉琴刘文庆仲崇超詹玉进
Owner GENCHEM & GENPHARM CHANGZHOU CO LTD
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