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Preparation method of FAPGG

A compound, a furyl-based technology, applied in the field of organic synthesis for the preparation of FAPGG, can solve the problems of large environmental pollution, low total yield, high cost, etc., and achieve the effect of simple process, high yield and high purity

Active Publication Date: 2020-09-01
CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The cost of this method is high, and the total yield is only 7.8%; DCC will release a part of DCU in the process of activating the carboxylate, and it is difficult to remove the residue in the product, and the DCC condensing agent causes great environmental pollution and is not conducive to industrialization. Production (see process route below)

Method used

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  • Preparation method of FAPGG
  • Preparation method of FAPGG
  • Preparation method of FAPGG

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] 1. Preparation of ethyl glycylidene hydrochloride. Into a 100mL three-necked flask, add 10.6g of diglyglyceride and 36.8g of absolute ethanol in sequence, cool to 0°C, slowly add 19.1g of thionyl chloride dropwise, after the addition is complete, stir and react at 40°C for 6h. The reaction mixture was rotary evaporated to remove the solvent, and then filtered to obtain a white solid, which was dried in vacuo at 40°C to obtain 15.0 g of a white solid with a yield of 94.9%. 1 HNMR (500 MHz, D 2 O), δ: 4.26~3.92(dd, J =15.0,5.0 Hz,2H),4.09~4.07(d, J =10.0 Hz,2H),3.92(s,2H),1.29~1.26(t, J =15.0,5.0 Hz,3H).

[0021] 2. Preparation of N-[3-(2-furyl)acryloyl]-L-phenylalanyl-glycyl-glycine ethyl ester. Into a 100mL three-necked flask, 5.7g N-[3-(2-furyl)acryloyl]-L-phenylalanine, 9.4g diglycidyl ethyl ester hydrochloride and 30mL of anhydrous dichloromethane were sequentially added, The mixture was cooled to 0°C, and under nitrogen, slowly added dropwise 11.9g of diisopro...

Embodiment 2

[0029] 1. The preparation of ethyl diglycopeptide hydrochloride. Into a 250mL three-neck flask, add 19.8g of diglyglyceride and 69.0g of absolute ethanol in sequence, cool to 0°C, slowly add 35.7g of thionyl chloride dropwise, after the addition is complete, stir and react at 40°C for 6h. The reaction mixture was rotary evaporated to remove the solvent, and the solid was obtained by filtration, and dried under vacuum at 40°C to obtain 28.2 g of a white solid, with a yield of 95.6%.

[0030] 2. Preparation of N-[3-(2-furyl)acryloyl]-L-phenylalanyl-glycyl-glycine ethyl ester. Add 14.3g N-[3-(2-furyl)acryloyl]-L-phenylalanine, 13.2g diglyceride ethyl ester hydrochloride and 80mL anhydrous dichloromethane to a 250mL three-necked flask successively, The mixture was cooled to 0°C, and under nitrogen, slowly added dropwise 29.7g of diisopropylethylamine (adjusted to pH 9) and BOP (44.3g) in dichloromethane solution, the dropwise addition was complete, and the reaction was The react...

Embodiment 3

[0033] 1. The preparation of ethyl diglycopeptide hydrochloride. Into a 250mL three-neck flask, add 33.0g of diglyglyceride and 115.0g of absolute ethanol in sequence, cool to 0°C, slowly add 59.5g of thionyl chloride dropwise, after the addition is complete, stir and react at 40°C for 6h. The reaction mixture was rotary evaporated to remove the solvent, and the solid was obtained by filtration, and dried under vacuum at 40°C to obtain 46.6 g of a white solid, with a yield of 94.9%.

[0034] 2. Preparation of N-[3-(2-furyl)acryloyl]-L-phenylalanyl-glycyl-glycine ethyl ester. Add 28.5g N-[3-(2-furyl)acryloyl]-L-phenylalanine, 39.3g diglyceride ethyl ester hydrochloride and 150mL anhydrous dichloromethane to a 250mL three-necked flask successively, The mixture was cooled to 0°C, and under nitrogen, slowly added dropwise 59.3g of diisopropylethylamine (adjusted to pH 9) and a solution of BOP (88.4g) in dichloromethane. After the addition was complete, the reaction was The react...

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Abstract

The invention discloses a preparation method of N-[3-(2-furyl) acryloyl]-L-phenylalanyl-glycyl-glycine (FAPGG), and belongs to the technical field of organic synthesis. The preparation method comprises the following steps of: (1) letting thionyl chloride react with glycylglycine in ethanol to obtain glycylglycine ethyl ester hydrochloride; (2) dissolving N-[3-(2-furyl) acryloyl]-L-phenylalanine and glycylglycine ethyl ester hydrochloride into dichloromethane, and reacting under the conditions of organic alkali and a condensing agent to obtain N-[3-(2-furyl) acryloyl]-L-phenylalanyl-glycyl-glycine ethyl ester; and (3) dissolving N-[3-(2-furyl) acryloyl]-L-phenylalanyl-glycyl-glycine ethyl ester in an organic solvent, and hydrolyzing under an alkaline condition to obtain the FAPGG. FAPGG isan important substrate for determining the activity of angiotensin converting enzyme, and can be used for diagnosing hypertension, diseases in lung, kidney, liver and thyroid and other diseases. The synthetic method disclosed by the invention is short in route, simple in process and repeatable, and the obtained product is high in purity, high in yield and suitable for industrial production and hasimportant economic and social benefits.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and relates to an organic synthesis method for preparing FAPGG. Background technique [0002] Hypertension is the most common cardiovascular disease in the world. Patients have no obvious symptoms in the early stage, and generally do not attract the attention of patients until the onset of the disease shows strong discomfort. Therefore, it is called the "invisible killer" of human health . According to the statistics of relevant departments, there are as many as 800 million people with high blood pressure in the world, of which about 200 million people are in China. Therefore, the detection and treatment of high blood pressure has become one of the health problems that need to be solved urgently in the world. There are many factors that cause hypertension, among which the regulation of angiotensin-converting enzyme (ACE) in the human body is considered to be one of the most important fa...

Claims

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Application Information

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IPC IPC(8): C07K5/087C07K1/02
CPCC07K5/0812Y02P20/55
Inventor 黄朋勉陈金星吕彦博王梓鉴周胜周智慧段湘生熊前政
Owner CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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