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Method for preparing O-tert-butyl-L-threonine tert-butyl ester

A technology of tert-butyl threonine and tert-butyl, applied in the field of peptide and protein synthesis, can solve the problems of high energy consumption, hidden dangers, unfavorable transportation and storage, etc., and achieve the effect of simple process

Inactive Publication Date: 2020-02-14
熊飞龙
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the boiling point of isobutene is -6.9°C, and in order to maintain a homogeneous reaction, it is necessary to add isobutene at a low temperature of -50°C. The high equipment requirements and high energy consumption are not conducive to industrial production, and isobutene is a flammable and explosive gas. It is not conducive to transportation and storage, which brings great safety hazards to production, and has no benefit to the cost reduction of industrial production and environmental protection requirements

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] The preparation method of ZSM-5 loaded silicotungsten solid acid catalyst is as follows:

[0023] 1) Dissolve the molar ratio of 1mol silicate and 1mol tungstate in 1.5L distilled water, mix well, add 500g ZSM-5 molecular sieve, ultrasonically disperse for 3 minutes, stir and react for 3 hours, add liquid acid to make the pH of the reaction solution The value is 1, heated to 60°C to continue the reaction for 3 hours, fully load the silicate ions and tungstate ions on the ZSM-5 molecular sieve, and filter to obtain the catalyst precursor;

[0024] 2) The catalyst precursor obtained in step 1) is first washed with 0.1mol / L dilute hydrochloric acid, then washed with deionized water, then vacuum-dried at 80-100°C, and calcined at 400-500°C for 3-5 hours to obtain ZSM-5 supports silicotungstic acid catalyst.

Embodiment 2

[0026] (1) Add L-threonine (119) and 0.5-2% ZSM-5 loaded silicotungstic acid solid acid catalyst into organic solvents THF, 1,4 dioxane, DMSO, DMF, and stir well Add the first batch of 1.1-2 moles of butylation reagent tert-butanol or tert-butyl methyl ether, raise the temperature to 30-50°C and react for 3-10 hours, then raise the temperature to 50-70°C, add the second batch of 1.5-3 moles of butyl Base reagent tert-butanol or tert-butyl methyl ether, continue to keep warm for 5-10 hours;

[0027] (2) After the reaction, remove the solid acid catalyst by filtration, wash the filtrate with water and saturated brine, dry over anhydrous sodium sulfate, filter, concentrate, and distill under reduced pressure to collect 70°C / 0.05mmHg fractions to obtain O-tert-butyl -L-threonine tert-butyl ester.

Embodiment 3

[0029] (1) Add L-threonine (119) and 0.5-2% ZSM-5 loaded silicotungstic acid solid acid catalyst into organic solvents THF, 1,4 dioxane, DMSO, DMF, and stir well Add the first batch of 1.1-2 moles of butylation reagent tert-butanol or tert-butyl methyl ether, raise the temperature to 30-50°C and react for 3-10 hours, then raise the temperature to 50-70°C, add the second batch of 1.5-3 moles of butyl Base reagent tert-butanol or tert-butyl methyl ether, continue to keep warm for 5-10 hours;

[0030] (2) After the reaction, remove the solid acid catalyst by filtration, wash the filtrate with water and saturated brine, dry over anhydrous sodium sulfate, filter, concentrate, and distill under reduced pressure to collect 70°C / 0.05mmHg fractions to obtain O-tert-butyl -L-threonine tert-butyl ester.

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Abstract

The invention relates to a method for preparing O-tert-butyl-L-threonine tert-butyl ester. A ZSM-5 supported silicotungstic acid catalyst is selected, tert-butyl alcohol or tert-butyl methyl ether isused as a butylation reagent, and the O-tert-butyl-L-threonine tert-butyl ester preparation method suitable for industrial production is provided through step-by-step reaction conditions; the yield ofthe preparation method is larger than 80%, the purity is larger than 99%, and the preparation method is simple in process and suitable for industrial production requirements.

Description

technical field [0001] The invention belongs to the field of polypeptide and protein synthesis, in particular to a method for preparing O-tert-butyl-L-threonine tert-butyl ester. Background technique [0002] O-tert-butyl-L-threonine tert-butyl ester is an important raw material for the synthesis of polypeptides and proteins. In the synthesis of polypeptides, because amino acid tert-butyl ester is easily decomposed by acid, it is often used as a carboxyl protecting group to participate in reaction. Amino acid tert-butyl ester can be prepared from the reaction of amino acid with tert-butyl acetate and perchloric acid, or from the reaction of amino acid with isobutylene in a mixture of dioxane and concentrated sulfuric acid. The latter reaction is simple and easy to operate. [0003] U.S. Patent US4601852 discloses the application of O-tert-butyl-L-threonine tert-butyl ester in artificially synthesizing human insulin. At present, domestic and foreign reports synthesize the me...

Claims

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Application Information

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IPC IPC(8): C07C227/16C07C227/18C07C227/40C07C229/22B01J29/48
CPCB01J23/002B01J29/48B01J2229/186C07C227/16C07C227/18C07C227/40C07C229/22
Inventor 熊飞龙
Owner 熊飞龙
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