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Method for preparing (S)-2-aminocyclopropylacetic acid

A technology of glycolic acid and amino ring, which is applied in the field of preparation of 2-aminocyclopropylacetic acid, can solve the problems of difficult industrial production, expensive raw materials, long routes, etc., and achieve the effect of simple and optimized synthetic process route and low cost

Inactive Publication Date: 2012-09-19
SYNCOZYMES SHANGHAI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw materials used in this method are expensive, the route is long, and the highly toxic drug KCN is also used, so industrial production is very difficult

Method used

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  • Method for preparing (S)-2-aminocyclopropylacetic acid
  • Method for preparing (S)-2-aminocyclopropylacetic acid
  • Method for preparing (S)-2-aminocyclopropylacetic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Synthetic route see image 3 .

[0029] step 1

[0030] Add 60mL of water and sodium carbonate solid particles (138mg, 0.012eq.) into a 1L three-necked flask, stir to dissolve it, and then slowly add the substrate cyclopropyl methyl ketone (9.1g, 10.72mL, 108.2mmol), to The mixture was heated until the internal temperature reached 50°C. At this time, the aqueous solution of potassium permanganate (34.2g, 216.4mmol, 1500mL), which had been heated to 80°C and dissolved, was slowly added dropwise with a constant pressure dropping funnel until the addition was completed. Finally, the balloon was covered with the mouth of the bottle, and the reaction was carried out overnight at 50°C. After cooling the reaction solution to room temperature, add methanol (60mL) and stir for a few minutes, then filter with celite, wash with hot water once, adjust the pH value of the filtrate to 5-6, extract with DCM (6X), and use anhydrous sulfuric acid for the organic layer After the magne...

Embodiment 2

[0035] Synthetic route see image 3 .

[0036] step 1

[0037]Add 60mL of water and sodium hydroxide solid particles (48mg, 0.012eq.) into a 1L three-necked flask, stir to dissolve, and then slowly add the substrate cyclopropyl methyl ketone (9.1g, 10.72mL, 108.2mmol), Heat the mixture until the internal temperature reaches 60°C, then slowly add a solution of potassium permanganate (51.3g, 324.6mmol, 1500mL) that has been heated to 50°C dropwise with a constant pressure dropping funnel until the addition is complete Finally, the balloon was covered with the mouth of the bottle, and the reaction was carried out overnight at 50°C. After cooling the reaction solution to room temperature, add methanol (60mL) and stir for a few minutes, then filter with celite, wash with hot water once, adjust the pH value of the filtrate to 5-6, extract with DCM (6X), and use anhydrous sulfuric acid for the organic layer After the magnesium was dried, it was concentrated under reduced pressure,...

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Abstract

The invention relates to a method for preparing a (S)-2-aminocyclopropylacetic acid. The method includes two sequentially processed steps that step one, cyclopropyl methyl ketone which serves as a raw material is subjected to an oxidation reaction to generate 2-cyclopropyl ketonic acid and / or 2-cyclopropyl keto acid salts; and step two, an obtained product from the step one is subjected to a dehydrogenation reaction with a solution containing ammonium ions and formate ions under the action of leucine dehydrogenase to generate the (S)-2-aminocyclopropylacetic acid. Compared with methods in prior art, cheap cyclopropyl methyl ketone is utilized by the technical scheme as the raw material, two steps of a chemical method and an enzyme method are combined to prepare the (S)-2-aminocyclopropylacetic acid, the synthesis process route is concise and optimized, the cost is low, and the method is high efficient and suitable for industrial production.

Description

technical field [0001] The invention relates to a method for preparing (S)-2-aminocyclopropylacetic acid. Background technique [0002] Unnatural amino acids are a very important class of organic compounds, many of which have biological activity and are often used as chemical raw materials and pharmaceutical intermediates. In particular, cyclopropyl-containing unnatural amino acids are widely used in drug synthesis (see document J.Med.Chem.(2011), 54(24), 8305-8320; Bioorg. & Med.Chem.Lett.(2006 ), 16, 1780–1783 and US Patent US20110237636, etc.). [0003] 2-Aminocyclopropylacetic acid (alias cyclopropylglycine, referred to as CPG; CAS: 49606-99-7) is a non-natural amino acid containing cyclopropyl group. It has good water solubility and a melting point of 189°C. Isomers: (S)-2-aminocyclopropylacetic acid (L-cyclopropylglycine, (S)-CPG) and (R)-2-aminocyclopropylacetic acid (D-cyclopropylglycine, ( R)-CPG). [0004] 2-Aminocyclopropylacetic acid is an important biomedica...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P13/04
Inventor 文军孙勇王献周江城松
Owner SYNCOZYMES SHANGHAI
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