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Method for preparing chiral isoquinoline carboxylic acid

A technology of isoquinoline carboxylic acid and isoquinoline carboxylic acid ester, which is applied in the field of preparation of chiral isoquinoline carboxylic acid, can solve problems that have not been seen, and achieve the effects of high production rate, good selectivity and simple process

Pending Publication Date: 2019-06-18
TONGLI BIOMEDICAL +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there is no report on the synthesis of (R)-1-TIC

Method used

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  • Method for preparing chiral isoquinoline carboxylic acid
  • Method for preparing chiral isoquinoline carboxylic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Preparation and separation of embodiment 1 (R)-1-TIC

[0025] Preparation of (R)-1-TIC:

[0026] Preparation of substrate solution: 10 g / L racemate solution of 1-TIC ester was prepared with 0.1 M aqueous ammonium acetate buffer (pH=8.0) and the initial pH value of the solution was adjusted to 8.0 with 30% ammonia water.

[0027] Transfer 300mL of the prepared substrate solution to a round-bottomed flask, set an external constant temperature heating water bath, add QLlip-9 to the substrate solution until the content of QLlip-9 is 5g / L, and react at 30°C for 6h. During the process, the pH value of the reaction solution was always adjusted to be about 8.0 by adding 30% ammonia water. At the end of the reaction, take a certain amount of hydrochloric acid to adjust the reaction solution to be strongly acidic to terminate the reaction, transfer the entire reaction solution to a volumetric flask, use the mobile phase to constant volume, dilute a certain number of times, then ...

Embodiment 2

[0030] Preparation and separation of embodiment 2 (R)-1-TIC

[0031] Preparation of (R)-1-TIC:

[0032] Preparation of substrate solution: 10 g / L racemate solution of 1-TIC ester was prepared with 0.1 M aqueous ammonium acetate buffer (pH=8.0) and the initial pH value of the solution was adjusted to 8.0 with 30% ammonia water.

[0033] Transfer 1000mL of the prepared substrate solution to the reaction container, set an external constant temperature heating water bath, add QLlip-9 to the substrate solution until the content of QLlip-9 is 5g / L, and react at 30°C for 6h, during the reaction process The pH value of the reaction solution was adjusted to always be about 8.0 by adding 30% ammonia water. At the end of the reaction, take a certain amount of hydrochloric acid to adjust the reaction solution to be strongly acidic to terminate the reaction, transfer the entire reaction solution to a volumetric flask, use the mobile phase to constant volume, dilute a certain number of tim...

Embodiment 3

[0036] Preparation and separation of embodiment 3 (R)-1-TIC

[0037] Preparation of (R)-1-TIC:

[0038]Preparation of substrate solution: 10 g / L racemate solution of 1-TIC ester was prepared with 0.1 M aqueous ammonium acetate buffer (pH=8.0) and the initial pH value of the solution was adjusted to 8.0 with 30% ammonia water.

[0039] Transfer 20,000 mL of the prepared substrate solution to a reaction vessel, stir the reactor with an external insulation jacket, add QLlip-9 to the substrate solution until the content of QLlip-9 is 5 g / L, and react at 30°C for 6 hours, During the reaction, the pH value of the reaction solution was adjusted to be about 8.0 by adding 30% ammonia water. At the end of the reaction, take a certain amount of hydrochloric acid to adjust the reaction solution to be strongly acidic to terminate the reaction, transfer the entire reaction solution to a volumetric flask, use the mobile phase to constant volume, dilute a certain number of times, then filter...

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Abstract

The invention discloses a method for preparing chiral isoquinoline carboxylic acid (I). The method comprises following steps: racemate of a compound I is subjected to a reaction to produce the compound shown as (I) in an aqueous phase buffer solution and under the catalysis of candida antarctica lipase B, the reaction is required to be always carried out at a preset pH value, and the preset pH value is 7.8-8.2. The method has the characteristics that the reaction condition is mild, stereoselectivity is high, reaction efficiency is high, and the technology is relatively simple and the like andhas industrial application prospects.

Description

technical field [0001] The invention belongs to the technical field of biocatalysis, and in particular relates to a method for preparing chiral isoquinoline carboxylic acid. Background technique [0002] Tetrahydroisoquinoline (THIQ) skeleton is an important structural module of many drugs such as trabectedine, narcotine, quinapril and praziquantel. Novel THIQ therapeutics have received increasing attention due to their specific anticancer, anti-inflammatory and immunological activities, for example, (R)-1-methyl-6,7-dihydroxy-1,2,3 , 4-tetrahydroisoquinoline and 1-methyl-1,2,3,4-tetrahydroisoquinoline are important intermediates for the synthesis of novel therapeutic agents for Parkinson's disease. As a class of unnatural bicyclic amino acids, 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (1-TIC) can be used to develop bioactive peptides such as antimicrobial peptides (AMPs) for innate immune protection . In addition, 1-TIC can replace phenylalanine synthetic farnesyl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P17/12
CPCC12P17/12C12Y301/01003
Inventor 吴坚平汤灵娇詹晓杨立荣钱明心
Owner TONGLI BIOMEDICAL
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