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Synthesis method of (S)-amino compound

A technology of amino compounds and compounds, applied in organic chemistry methods, organic chemistry, etc., can solve the problems of expensive chiral starting materials, unfavorable industrial production, and increased synthesis costs

Active Publication Date: 2021-08-24
迪嘉药业集团股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The chiral starting materials used in the synthesis method reported in Scheme 4 are expensive, which will greatly increase the synthesis cost, and the reaction uses strong reducing conditions, which is not conducive to industrial production

Method used

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  • Synthesis method of (S)-amino compound
  • Synthesis method of (S)-amino compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Preparation of Compound 16

[0071] Take 1000 ml of three bottles, add o-amino-aminoceal (100.23 g, 825 mmol), pyruvate (87.23 g, 991 mmol) and drinking water (500.00 g, 5 times the mass of o-amino), temperature control 20 ~ 30 o C, then add potassium hydroxide (111.16 g, 1.98 mol) in batch to the reaction system, temperature control temperature 20 to 30 during hydrogenated potassium hydroxide o C; after the addition, the temperature control temperature is 20 ~ 30 o C reaction 2H, after the reaction, the pH of the reaction system is adjusted to 4 to 5 after the reaction is completed, and there will be a large amount of solid formation during the tuning pH; filter, filter cake with 100.00 g Drinking water and 1155 ~ 65 o C Heaves dry 10 h. Compound 16, mass of 155.46 g, HPLC purity: 99.34%, yield: 98.5% ,.

[0072] Preparation of Compound 17

[0073] The 2 L high pressure reactor was taken into a compound 16 (140.00 g, 732 mmol), methanol (700.00 g, the compound 16 mass of t...

Embodiment 2

[0081] Preparation of Compound 16

[0082] Take 1000 ml of three bottles, add o-amino-aminoceraldehyde (100.00 g, 825 mmol), pyruvate (72.69 g, 825 mmol) and drinking water (500.00 g, 5 times the mass of o-amino), temperature control 20 ~ 30 o C, then add potassium hydroxide (111.16 g, 1.98 mol) in batch to the reaction system, temperature control temperature 20 to 30 during hydrogenated potassium hydroxide o C; after the addition, the temperature control temperature is 20 ~ 30 o C reaction 2H, after the reaction, the pH of the reaction system is adjusted to 4 to 5 after the reaction is completed, and there will be a large amount of solid formation during the tuning pH; filter, filter cake with 100.00 g Drinking water and 1155 ~ 65 o C Heaves dry 10 h. The compound 16 was obtained as 142.99 g, yield: 90.6%, HPLC purity: 99.08%.

[0083] Preparation of Compound 17

[0084] A 2 L high pressure reactor was added to the compound 16 (140.00 g, 732 mmol), methanol (700.00 g, the compoun...

Embodiment 3

[0092] Preparation of Compound 16

[0093] Take 1000 ml of three bottles, incorporate an o-amino-aminoceal (100.00 g, 825 mmol), pyruvate (87.23 g, 991 mmol) and drinking water (500.00 g, 5 times the compound of the compound), temperature control 20 to 30 o C, then add sodium hydroxide (79.25 g, 1.98 mol) in a reaction system, temperature control temperature in the process of hydroxide, 20 ~ 30 o C; after the addition, the temperature control temperature is 20 ~ 30 o C reaction 2H, after the reaction, the pH of the reaction system is adjusted to 4 to 5 after the reaction is completed, and there will be a large amount of solid formation during the tuning pH; filter, filter cake with 100.00 g Drinking water and 1155 ~ 65 o C Heaves dry 10 h. The compound 16 was obtained as 148.83 g, yield: 94.3%, HPLC purity: 99.12%.

[0094] Preparation of Compound 17

[0095] A 2 L high pressure reactor was added to the compound 16 (140.00 g, 732 mmol), methanol (700.00 g, 5.00 g / g) and PD / C (...

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Abstract

The invention relates to a synthesis method of a benazepril hydrochloride intermediate (S)-amino compound. According to the technical scheme, the preparation method of the (S)-amino compound comprises the following steps of by taking 2-aminobenzaldehyde 15 as an initial raw material, carrying out Aldol condensation under the action of alkali to prepare a compound 16, carrying out Pd / C catalytic hydrogenation on the compound 16 to prepare a compound 17, and carrying out DCC condensation on the compound 17 to generate a main structure compound 18 of the benazepril intermediate (S)-amino compound, carrying out substitution reaction on the compound 18 and tert-butyl chloroacetate to prepare a compound 19, and carrying out transamination reaction on the compound 19 under the catalytic action of a quinine-derived catalyst to generate the benazepril intermediate (S)-amino compound 1. The benazepril intermediate (S)-amino compound is synthesized by a method for directly constructing a chiral center through asymmetric catalysis, so that the reaction yield is increased.

Description

Technical field [0001] The present invention designs a benapilian intermediate for hydrochloride ( S ) - Synthesis of amino compounds, in a further, the present invention relates to a kind of S Synthesis of-3-amino-2,3,4,5-tetrahydro-2-oxo-1H-1-benzoxazone-1-acetate tert-butyl ester. Background technique [0002] Cardiovascular disease is the most common type of disease in humans. According to the World Health Organization report, cardiovascular disease is the first cause cause of the world's population. Precursive drugs for the treatment of high blood pressure are mainly four categories: diuretics, calcium antagonists, angiotensin converting enzyme inhibitors (ACEI) and vascular tension II receptor antagonists. [0003] BenazePril Hydrochloride is an oral long-acting, ineffective angiotensin converting enzyme (ACE) inhibitor developed by Novatt Pharmaceutical Company, Switzerland, has been listed in Denmark in 1990, followed by Japan, Germany. In dozens of countries such as Fran...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D223/16
CPCC07D223/16C07B2200/07
Inventor 张启超苗华明葛执信李晶刘宇
Owner 迪嘉药业集团股份有限公司
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