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Synthesis process of compound D-2- aminoxy-3-methylbutyric acid

A technology of methyl butyric acid and D-2- is applied in the field of synthesis technology of the compound D-2-aminooxy-3-methyl butyric acid, and can solve the problem that optically active raw materials are not readily available, have no stereoselectivity, Control the problem of poor product effect, and achieve the effect of low price, easy control and low synthesis cost

Inactive Publication Date: 2013-02-06
GANSU RES INSTION OF CHEM IND GRICI
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

However, these methods have obvious shortcomings, mainly reflected in the fact that these methods are not effective in controlling the chirality of the product, either because optically active raw materials are not easy to obtain, or the reaction itself has no stereoselectivity

Method used

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Embodiment Construction

[0023] The synthesis of the D-2-aminooxy-3-methylbutanoic acid compound of the present invention will be further illustrated by specific examples below.

[0024] (1) Synthesis of compound (S)-2-hydroxy-3-methylbutanoic acid (Ⅱ)

[0025] 40mL concentrated H 2 SO 4 Add 1300 mL of water, add 0.5 mol of L-valine, add NaNO dropwise under ice bath 2 Solution (1.5 mol / 300 mL water), control temperature less than 5°C, NaNO 2 After the dropwise addition, the stirring reaction was continued for 1.5 hours, and the ice bath was removed and gradually returned to room temperature for 2 hours of reaction. Stop the reaction, extract with ethyl acetate (1000 mL×4), wash with brine (400 mL), and back-extract the brine twice with ethyl acetate, add anhydrous NaSO to the collected organic phase 4 After drying, filtering and evaporating ethyl acetate to obtain compound (II), the crude product was directly put into the next reaction without purification.

[0026] (2) Synthesis of compound (S...

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Abstract

The invention discloses a synthesis process of compound D-2- aminoxy-3-methylbutyric acid, and belongs to the technical field of chemical synthesis. The synthesis process includes taking natural amino acid L-valine as a raw material, and then synthetizing the non-natural D-2- aminoxy-3-methylbutyric acid by steps of diazotization hydrolysis, acetyl protection, tert-butyl esterification, deacetylation, Mitsunobu reaction, dephthaloyl, tert-butyl ester hydrolysis and the like. The compound is synthetized by raw materials easy to obtain and is low-price; synthesis operations are convenient and simple, reaction conditions are mild and easy to control, reaction selectivity is good, yield is high, and accordingly the compound is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and relates to a synthesis process of compound D-2-aminooxy-3-methylbutanoic acid. Background technique [0002] D-2-aminooxy-3-methylbutyric acid is a new type of peptidomimetic structural unit, which is obtained by replacing the carbon atoms on the corresponding natural amino acid carbon skeleton with oxygen atoms. It has physiological activity and can form a right-handed α The N—O rotation angle can be used in the design of chiral shift reagents for carboxylic acids. It has high accuracy and reliability in the measurement of enantiomeric excess of carboxylic acids, and the peptoids synthesized from it have the same natural activity. Peptides have the same activity and are not easily degraded by enzymes in the body, so they are widely used in the design and synthesis of new drugs. The structural formula of D-2-aminooxy-3-methylbutanoic acid is as follows: [0003] [0004] D-2-a...

Claims

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Application Information

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IPC IPC(8): C07C291/04
Inventor 彭维恩武林焕张鹏云
Owner GANSU RES INSTION OF CHEM IND GRICI
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