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Method for synthesizing N-tert-butoxy-oxo-L-isoleucine

A technology of tert-butoxycarbonyl and isoleucine, which is applied in the chemical industry, can solve problems such as high product cost, high price, and long process time, and achieve the effects of reducing production costs, shortening production cycles, and improving production efficiency

Inactive Publication Date: 2006-08-09
BAOSHENG BIOLOGICAL CHEM YANGZHOU
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  • Description
  • Claims
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Problems solved by technology

This synthetic method has the following disadvantages: first, the raw material used is BOC azide, which can only be supplied as a reagent in the market, and cannot be purchased in batches, and the price is very high, which cannot meet the requirements of N-tert-butoxycarbonyl-L-isobright The industrialized production of amino acid needs; The 2nd, the time of dripping NaOH solution is 2 days, and the process time of this step is too long, prolongs the cycle of industrialized production; The 3rd, product yield is 79.2% (with L-isoleucine acid meter), the yield is low, and the product cost is too high, which is not conducive to commercial sales

Method used

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  • Method for synthesizing N-tert-butoxy-oxo-L-isoleucine
  • Method for synthesizing N-tert-butoxy-oxo-L-isoleucine

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Embodiment Construction

[0012] The present invention synthesizes N-tert-butoxycarbonyl-L-isoleucine, the main raw material that adopts is L-isoleucine, BOC acid anhydride and 50% dioxane aqueous solution, and the mol ratio of raw material is 1: 1.66:7.22, the procedure is as follows: 131.18 grams of L-isoleucine, 218 grams of BOC anhydride and 960 grams of 50% dioxane aqueous solution are placed in the reactor and stirred to fully dissolve the L-isoleucine After putting into ice brine to cool, the chemical reaction equation is:

[0013]

[0014] Add 4N sodium hydroxide aqueous solution dropwise for 2 hours to maintain the pH value of the reaction system at 9-10. When the pH value is constant at 9, the reaction is terminated and the temperature is controlled at 15-25°C;

[0015] Extract twice with 900 mL of ethyl acetate, leave a layer of water, add hydrochloric acid to make the pH value of the solution 9, the chemical reaction equation is:

[0016]

[0017] Extract twice with 900 mL of ethyl a...

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Abstract

The invention relates to N-boc-L-isoleucine synthetic method. It belongs to chemical engineering technique field. Its features are as follows: using BOC acid anhydride as raw material to increase production efficiency, reduce production cost; adding NaOH solution to shorten production cycle; the yield of L-isoleucine can reach 105.2% which is higher than literature disclosed for over 20%.

Description

technical field [0001] The invention relates to a method for synthesizing N-tert-butoxycarbonyl-L-isoleucine in the technical field of chemical industry. Background technique [0002] N-tert-butoxycarbonyl-L-isoleucine is a key raw material for synthesizing polypeptides and drugs. The third volume of "Modern Chemical Reagent Handbook" Biochemical Reagents (1) discloses that 26 grams of L-isoleucine are suspended in 80M water and dioxane (1:1) solution, add 28.6 grams of BOC (ie tert-butoxycarbonyl) azide under stirring, adjust the pH value to 9.8 with NaOH, add dropwise for 2 days, the reaction is yellow and transparent, use Extract with ethyl acetate, acidify the aqueous layer, extract with ethyl acetate, wash with sodium chloride solution, dry over anhydrous sodium sulfate, concentrate under reduced pressure, obtain crystals overnight, and dry to obtain 20.6 g of the finished product. This synthetic method has the following disadvantages: first, the raw material used is B...

Claims

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Application Information

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IPC IPC(8): C07C271/22C07C269/00
Inventor 张明宝
Owner BAOSHENG BIOLOGICAL CHEM YANGZHOU
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