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Preparation of medical intermediate AMD by electro-reduction

A technology of diethyl acetamidomalonate and diethyl nitrosomalonate, which is applied in the new process field of preparing pharmaceutical intermediate AMD, and can solve the problems of high price, low yield and rising synthesis cost, etc. problem, to achieve the effect of increasing product yield and reducing production cost

Inactive Publication Date: 2010-04-07
安徽省恒锐新技术开发有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

With Pd-C and Pt-C, either the yield is not high, or the reaction time is too long; and the use of Pt-C catalyst is expensive
At present, the industry also uses diethyl nitrosomalonate as a raw material, adding zinc powder to the acetic acid system to reduce it to diethyl aminomalonate. The method is simple, but as the price of zinc powder continues to rise, the synthetic The cost has risen sharply, and the advantages of this process no longer exist, so it is imperative to seek a low-cost production process for AMD

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The preparation of step 1 nitrosomalonate diethyl

[0027] Add 130ml of diethyl malonate (0.8mol), 35g (0.8mol) of sodium nitrite, 6ml of water and 190ml of toluene into a 1000ml three-necked flask, and dropwise add 80ml of glacial acetic acid below 5°C. After the dropwise addition, slowly raise the temperature to 40-50°C, react for 6 hours, then add water to dissolve the unreacted salt, pour it into a separatory funnel, wash the organic layer with 5% NaCl aqueous solution, discard the water layer, evaporate The toluene solvent of the organic layer was removed to obtain 145.2 g of a light yellow oily liquid with a purity of 98.5% and a yield of 96.0% (calculated as diethyl malonate).

[0028] Step 2 Electroreduction of diethyl nitrosomalonate and preparation of AMD

[0029] Anode: 0.5N NaSO 4 Solution 3000ml; cathode: buffer solution (PH=4-5) of sodium acetate and acetic acid 2500ml.

[0030] Sodium acetate, acetic acid buffer solution (PH = 4-5), add the above 76g n...

Embodiment 2

[0032] The preparation of step 1 nitrosomalonate diethyl

[0033] Same as Step 1 of Example 1.

[0034] Step 2 Electroreduction of diethyl nitrosomalonate and preparation of AMD

[0035] Anode: 0.5N NaSO 4 Solution 3000ml; cathode: buffer solution (PH=4-5) of sodium acetate and acetic acid 2500ml.

[0036] Sodium acetate, acetic acid buffer solution (PH = 4-5), add the above 76g nitrosomalonate diethyl ester (0.4mol) at 30-40 ℃, pass through a DC voltage of 5-6 volts for electric Reduction, point plate, when the raw material point disappears and the reaction reaches the end point, diethyl aminomalonate is obtained through extraction, and its purity is ≥99%. The obtained diethyl aminomalonate and 36 g of glacial acetic acid (0.6 mol) were mixed evenly, and 81.6 g of acetic anhydride (0.8 mol) was slowly added dropwise, and the feeding temperature was controlled at 40-50° C. After dripping, continue to keep warm and stir for 0.5-3 hours, and recover acetic acid by distillati...

Embodiment 3

[0038] The preparation of step 1 nitrosomalonate diethyl

[0039] Same as Step 1 of Example 1.

[0040] Step 2 Electroreduction of diethyl nitrosomalonate and preparation of AMD

[0041] Anode: 0.5N NaSO4 Solution 3000ml; cathode: buffer solution (PH=4-5) of sodium acetate and acetic acid 2500ml.

[0042] Sodium acetate, acetic acid buffer solution (PH = 4-5), add the above 76g nitrosomalonate diethyl ester (0.4mol) at 30-40 ℃, pass through a DC voltage of 5-6 volts for electric Reduction, point plate, when the raw material point disappears and the reaction reaches the end point, diethyl aminomalonate is obtained through extraction, and its purity is ≥99%. The obtained diethyl aminomalonate and 36 g of glacial acetic acid (0.6 mol) were mixed evenly, and 40.8 g of acetic anhydride (0.4 mol) was slowly added dropwise, and the feeding temperature was controlled at 40-50° C. After dripping, continue to keep warm and stir for 0.5-3 hours, and recover acetic acid by distillation...

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Abstract

Process for preparing AMD as medical intermediate from diethyl malonate is carried out by: preparing nitroso-diethyl malonate from diethyl malonate and sodium nitrite, using sodium acetate and sodiumsulfate and acetic acid as electrolyte, electrically reducing to prepare amino-diethyl malonate in frame bath with membranes, and acidating the reduced products to obtain AMD. It is simple and moderate, and has no pollution and high purity.

Description

1. Technical field [0001] The invention belongs to the field of pharmaceutical and chemical engineering, and relates to a new process for preparing a pharmaceutical intermediate AMD, especially a new process for preparing a pharmaceutical intermediate AMD with diethyl malonate as a raw material, which belongs to the reduction reaction preparation AMD technology field. 2. Background technology [0002] AMD is the abbreviation of diethyl acetamidomalonate, which is an important raw material and intermediate for organic synthesis and drug synthesis, especially in the synthesis of unnatural amino acids. With the development of the amino acid and peptide industry, the demand is increasing year by year, but due to technical limitations, the production of this product has not been able to meet the demand, and the demand gap in my country alone has reached nearly 1,000 tons. [0003] The AMD synthesis process routes that have been developed at home and abroad include the synthesis ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C25B3/04C25B3/25
Inventor 徐迈马云峰褚道葆袁希梅吴梅
Owner 安徽省恒锐新技术开发有限责任公司
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