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Method for preparing S-benzyl cysteinyl glycine ethyl ester under microwave condition

A technology of cysteinyl glycine ethyl ester and glycine ethyl ester hydrochloride, which is applied in the preparation of sulfides, organic chemistry, etc., can solve the problems of easy acid hydrolysis, difficult preservation of raw materials, and inability to obtain target products, etc. High efficiency, short reaction time and simple preparation method

Inactive Publication Date: 2010-12-01
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it was found through experiments that using benzyloxycarbonyl as a protecting group for this experiment, because S-benzyl-L-cysteine ​​contains a sulfur atom, will deactivate the Pa / C catalyst, and the desired target product cannot be obtained.
The acetic acid solution of hydrogen bromide is easy to change due to the volatile concentration of hydrogen bromide during the preservation process, and the raw materials are particularly difficult to preserve
In addition, in the acidic solution of hydrobromic acetic acid, it is easy to undergo acidic hydrolysis during deprotection to obtain by-products

Method used

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  • Method for preparing S-benzyl cysteinyl glycine ethyl ester under microwave condition
  • Method for preparing S-benzyl cysteinyl glycine ethyl ester under microwave condition
  • Method for preparing S-benzyl cysteinyl glycine ethyl ester under microwave condition

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Effect test

Embodiment 1

[0025] 1) Synthesis of S-benzyl-N-benzyloxycarbonylcysteinyl glycine ethyl ester

[0026] Glycine ethyl ester hydrochloride (2) 6.98g (0.05mol), was dissolved in 200ml of dichloromethane, and 20ml of tetrahydrofuran and 7ml of triethylamine were added to the solution, stirred to form a homogeneous solution, then 17.3g (0.05mol) was added ) S-benzyl-N-benzyloxycarbonyl cysteine ​​to form a uniform and transparent solution, control its temperature at about -2°C, and take another 10.5ml (0.05mol) of DCC and dissolve it in 50ml of dichloromethane, and stir Under certain conditions, slowly add it dropwise to the above-mentioned mixed solution of A and B, and control the dropping speed. After about 1 hour of dropping, keep it at -2°C for 5 hours. Remove N,N`-dicyclohexyl urea (DCU) by filtration, and the filtrate is washed with dilute HCl, NaHCO 3 Wash each time with anhydrous NaSO 4 Drying, concentration under reduced pressure, and solidification of petroleum ether gave 16.38 g o...

Embodiment 2

[0030] 1) same as embodiment 1;

[0031] 2) Synthesis of S-benzylcysteinyl glycine ethyl ester

[0032] Add 5g of S-benzyl-N-benzyloxycarbonylcysteinylglycine ethyl ester (3) in a 100ml three-necked flask equipped with a reflux condenser (a balloon is connected above the condenser to prevent hydrogen bromide from volatilizing too quickly), In a microwave instrument (built-in magnetic stirring), then add 25ml of 33% hydrogen bromide in acetic acid solution at 30°C, the reactant dissolves quickly and releases gas, the volume of the balloon expands, and after 15 minutes, part of the hydrogen bromide is pumped out under reduced pressure and glacial acetic acid to obtain an orange transparent liquid, add ether to wash to remove residual benzyl bromide, add water to the water layer and filter to remove insoluble matter, and freeze-dry the filtrate to obtain the product S-benzylcysteinylglycine ethyl ester (4): 2.83 g of slightly orange crystals, yield 82.3%.

Embodiment 3

[0034] 1) same as embodiment 1;

[0035] 2) Synthesis of S-benzylcysteinyl glycine ethyl ester

[0036] Add 5g of S-benzyl-N-benzyloxycarbonylcysteinylglycine ethyl ester (3) in a 100ml three-necked flask equipped with a reflux condenser (a balloon is connected above the condenser to prevent hydrogen bromide from volatilizing too quickly), In a microwave instrument (built-in magnetic stirring), then add 50ml of 33% hydrogen bromide in acetic acid solution at 30°C, the reactant dissolves quickly and releases gas, the volume of the balloon expands, and after 20 minutes, part of the hydrogen bromide is pumped out under reduced pressure and glacial acetic acid to obtain an orange transparent liquid, add ether to wash to remove residual benzyl bromide, add water to the water layer and filter to remove insoluble matter, and freeze-dry the filtrate to obtain the product S-benzylcysteinylglycine ethyl ester (4): 2.52 g of slightly orange crystals, yield 74.3%.

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Abstract

The invention relates to a method for preparing S-benzyl cysteinyl glycine ethyl ester under the microwave condition, which comprises the steps of: (1) dissolving glycine ethyl ester hydrochloride into methylene dichloride, adding tetrahydrofuran and triethylamine, then adding S-benzyl-N-benzoxy carbonyl cysteine, controlling the temperature to be -2 to 0 DEG C, additionally taking N, N'-dicyclohexyl carbodiimide DCC and dissolving in the methylene dichloride, and slowly dripping into the mixed solution under the stirring condition; and (2) adding S-benzyl-N-benzoxy carbonyl cysteinyl glycineethyl ester into a three-neck flask provided with a backflow condenser pipe and putting into a microwave instrument, then, adding saturated hydrogen bromide acetum, leading reactant to be rapidly dissolved, discharging gas, carrying reaction for 15-20min, reducing the pressure, extracting hydrogen bromide and glacial acetic acid, washing and drying. The method is simple, short in reaction time, high in yield and suitable for industrialized production.

Description

technical field [0001] The invention belongs to the field of synthesizing glutathione drug intermediates, in particular to a method for preparing S-benzylcysteinylglycine ethyl ester under microwave conditions. Background technique [0002] Glutathione is the most important non-protein sulfhydryl group and the most abundant low-molecular-weight polypeptide in mammalian cells. It is an antioxidant that protects the sulfhydryl groups of enzymes and other proteins, and participates in many functional activities in cells. Reduced glutathione can inhibit tumor growth and induce differentiation. Boehringer Mannhein is developing glutathione into a new drug for cancer treatment, and its preparation research is currently a hot spot. The production methods of glutathione mainly include biological fermentation method, enzymatic transfer method and chemical synthesis method. The content of strains in the microbial fermentation method is low, the extraction is difficult, and the yield...

Claims

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Application Information

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IPC IPC(8): C07C323/60C07C319/20
Inventor 钦维民徐秋霞王玮
Owner DONGHUA UNIV
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