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Synthesis method of 2,4-diaminobutyric acid derivative

A diaminobutyric acid and synthesis method technology, applied in the field of synthesis of 2,4-diaminobutyric acid derivatives, can solve the problems of troublesome post-processing and cumbersome steps, and achieve easy separation and purification, mild reaction conditions, and convenience for later stages Amplify the effect of production

Active Publication Date: 2021-03-09
NINGXIA MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction yield of this route is about 50%, but the steps are loaded down with trivial details, post-processing troubles, and limit its application

Method used

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  • Synthesis method of 2,4-diaminobutyric acid derivative
  • Synthesis method of 2,4-diaminobutyric acid derivative
  • Synthesis method of 2,4-diaminobutyric acid derivative

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preparation example Construction

[0036] The synthetic method of 2,4-diaminobutyric acid derivative comprises the following steps:

[0037] a. Dissolve homoserine in a mixed solvent, add an aqueous alkali solution, and drop di-tert-butyl dicarbonate solution dissolved in tetrahydrofuran at -5 to 5°C. After the addition, react at room temperature for 12 to 48 hours; the reaction is over Finally, the concentrated reaction solution was extracted with petroleum ether, the pH of the reaction solution was adjusted to 1-5 at -5-5°C, extracted with ethyl acetate, the extract was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and the organic layer was concentrated , column chromatography separation to obtain intermediate 1; the molar ratio of homoserine and di-tert-butyl dicarbonate is 1:1~1:2;

[0038] b. Mix intermediate 1 and triethylamine in an organic solvent, add benzyl bromide dropwise under reflux, and react for 4 to 8 hours after the dropwise addition; add water to the rea...

Embodiment 1

[0057] Embodiment 1 synthesis condition screening experiment

[0058] 1. Screening of ester hydrolysis conditions during the preparation of intermediate 4

[0059] The ester hydrolysis reagent that the present invention chooses initially is LiOH, NaOH, KOH, K 2 CO 3 and Na 2 CO 3 .

[0060] Intermediate 3 was mixed with the above-mentioned different ester hydrolysis reagents in 200 mL of methanol: water = 4: 1 (V / V) mixed solvent, and reacted at room temperature for 4 h. The reaction solution was spin-dried, adjusted to pH 1 with concentrated hydrochloric acid in an ice bath, extracted five times with dichloromethane (50 mL), washed once with saturated sodium chloride solution (50 mL), and dried over anhydrous sodium sulfate. Wherein, the molar ratio of intermediate 3 to each ester hydrolysis reagent is 1:20. The specific experimental results are shown in Table 1.

[0061] Table 1 Yield using different ester hydrolysis reagents

[0062] LiOH NaOH KOH K ...

Embodiment 2

[0071] Synthesis of Embodiment 2 Intermediate 1 (N-tert-butoxycarbonyl-homoserine)

[0072]

[0073] Dissolve homoserine (83.96mmol, 10.00g) in 250ml of ethanol: water = 2:1 (V / V) mixed system, add 84ml of 1N NaOH aqueous solution, stir the solution until it is clear and transparent, and place it in an ice bath A solution of di-tert-butyl dicarbonate (92.36 mmol, 20.16 g) dissolved in 84 ml of tetrahydrofuran was added dropwise, and after the addition was completed, the mixture was reacted at room temperature for 24 h.

[0074] The concentrated reaction solution was extracted 3 times with petroleum ether (100mL) to remove some impurities, the pH of the reaction solution was adjusted to 2 under ice bath, extracted 5 times with ethyl acetate (100mL), and the extract was washed once with saturated sodium chloride solution (30mL) , dried over anhydrous sodium sulfate. The organic layer was concentrated and separated by column chromatography (dichloromethane:methanol=2:1) ​​to ...

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Abstract

The invention belongs to the field of organic chemistry, and particularly relates to a synthesis method of a 2,4-diaminobutyric acid derivative. According to the synthesis method of the 2,4-diaminobutyric acid and the derivative thereof provided by the invention, homoserine is selected as an initial raw material, the amino and carboxyl of the homoserine are protected firstly, a pht group is introduced through a light delay reaction, and then a final product can be obtained through six steps of benzyl ester removal, pht removal and Boc group removal. According to the invention, the synthetic method provided by the invention has relatively high reaction yield and is convenient for separation and purification; the intermediates obtained in the reaction are all protecting group modified aminoacid derivatives and can be directly used as drug intermediates or raw materials for synthesizing other compounds, so that waste is avoided; and the reaction conditions provided by the invention are mild, and later-period amplification production is facilitated.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and specifically relates to a synthesis method of 2,4-diaminobutyric acid derivatives. Background technique [0002] 2,4-Diaminobutyric acid is a non-protein diamino acid originally isolated from sweet pea. This non-protein diamino acid has a wide range of biological activities, such as inhibiting the growth of fibrosarcoma cells. The multiple active groups and four-carbon structure of 2,4-diaminobutyric acid and its derivatives make it widely used as an intermediate in drug synthesis, such as the synthesis of ectoine with moisturizing activity as an intermediate. [0003] At present, the synthetic route of 2,4-diaminobutyric acid can be protected by Cbz (benzyloxycarbonyl) through the amino group of L-glutamine, and then degraded the amide bond with bis(trifluoroacetic acid) iodobenzene, and then hydrogenated to remove the Cbz protection get. The bis(trifluoroacetic acid) iodobenzene used in ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C269/04C07C271/22C07C269/06C07C271/18C07D209/48C07C227/18C07C227/20C07C229/26
CPCC07C269/04C07C269/06C07D209/48C07C227/18C07C227/20C07C271/22C07C271/18C07C229/26Y02P20/55
Inventor 黄宇郑佳安张晓洁樊艳茹
Owner NINGXIA MEDICAL UNIV
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