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Adamantyl amino-acid ester compound synthesis method

An adamantane amino acid ester and a synthesis method technology are applied in the field of synthesizing adamantane amino acid ester compounds, can solve the problems of insufficient stability and high cost, and achieve the effects of mild reaction conditions, low cost and simple reaction conditions

Inactive Publication Date: 2014-10-22
SHANGHAI INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The purpose of the present invention is mainly to provide a new synthetic method of adamantane amino ester compound in order to solve the shortcomings of high cost and insufficient stability in the biocatalytic amination process of ketoacids

Method used

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  • Adamantyl amino-acid ester compound synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] A kind of adamantyl amino ester compound, its structural formula is as follows:

[0033]

[0034] Wherein R is methyl, R' is OH.

[0035] The synthetic method of above-mentioned a kind of adamantyl amino ester compound specifically comprises the following steps:

[0036] (1) In a 50mL three-neck flask equipped with a thermometer, reflux condenser and vacuum plug, add 1.0g (4.2mmol) of compound 2, then add 21.0mL of solvent methanol and stir to dissolve completely, add 1.03g (8.4mmol) of compound 3 , after completely dissolving, add 0.09g (0.84mmol) triethylamine dropwise. After the addition is completed, the balloon is placed above the reflux condenser to isolate the air, and the reaction temperature is controlled at 60-65°C for 24 hours. Remove methyl alcohol, obtain imine compound crude product;

[0037] The structural formula of the compound 2 is as follows:

[0038] Wherein R is a methyl group, R' is a hydroxyl group, that is, compound 2 is (3-OH-1-adamantan...

Embodiment 2

[0049] A kind of adamantyl amino ester compound, its structural formula is as follows:

[0050]

[0051] Wherein R is methyl, R' is OH.

[0052] The synthetic method of above-mentioned a kind of adamantyl amino ester compound specifically comprises the following steps:

[0053](1) In a 50mL three-necked flask equipped with a thermometer, a reflux condenser and a vacuum plug, add 1.0g (4.2mmol) of compound 2, then add 21.0mL of solvent THF and stir to dissolve, add 1.03g (8.4mmol) of compound 3, After completely dissolving, add 0.09g (0.84mmol) triethylamine dropwise. After the addition is complete, put the balloon cover above the reflux condenser to isolate the air, and control the reaction temperature to 60-70°C for 24 hours. TLC detects that the basic reaction of the raw materials is complete. Rotary evaporation Remove tetrahydrofuran to obtain the imine compound crude product;

[0054] The structural formula of the compound 2 is as follows:

[0055] Wherein R is a m...

Embodiment 3

[0062] A kind of adamantyl amino ester compound, its structural formula is as follows:

[0063]

[0064] Wherein R is methyl, R' is OH.

[0065] The synthetic method of above-mentioned a kind of adamantyl amino ester compound specifically comprises the following steps:

[0066] (1) In a 50mL three-neck flask equipped with a thermometer, reflux condenser and vacuum plug, add 1.0g (4.2mmol) of compound 2, then add 21.0mL of solvent dichloromethane and stir to dissolve completely, add 1.03g (8.4mmol) After compound 3 was completely dissolved, 0.09g (0.84mmol) triethylamine was added dropwise. After the addition, the balloon was placed above the reflux condenser to isolate the air, and the reaction temperature was controlled at 30-40°C for 24 hours. TLC detected the raw material in the reaction. Residue, dichloromethane was removed by rotary evaporation to obtain the crude imine compound;

[0067] The structural formula of the compound 2 is as follows:

[0068] Wherein R i...

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Abstract

The invention discloses an adamantyl amino-acid ester compound synthesis method. The adamantyl amino-acid ester compound synthesis method has a structural formula shown in the description, wherein in the structural formula, R represents methyl, ethyl or isopropyl and R' represents H or OH. The adamantyl amino-acid ester compound synthesis method comprises the following steps that (3-R'-1-adamantyl)-2-oxoacetate and ortho-substituted benzylamine undergo a reaction in the presence of a catalyst at a temperature of 20-90 DEG C for 23-26h and the reaction product is subjected to rotary evaporation so that the solvent is removed and an imine compound crude product is obtained, the imine compound crude product is dissolved by tetrahydrofuran, the solution is acidized by HCl, the acidized solution is diluted by water, the dilute solution is washed by petroleum ether so that a petroleum ether layer is obtained, the petroleum ether layer is washed by 1N of HCl, the water layer is treated by NaHCO3 until a pH is 8, the water layer is exacted by methylene dichloride, the methylene dichloride layer is dried by anhydrous magnesium sulfate and then is filtered and concentrated, and the concentrate is purified by a silica gel chromatographic column so that an adamantyl amino-acid ester compound is obtained. The adamantyl amino-acid ester compound synthesis method has the advantages of low cost, simple and mild reaction conditions and good reappearance.

Description

technical field [0001] The invention relates to a method for synthesizing an adamantane amino acid ester compound. Background technique [0002] In July 2009, Saxagliptin (Saxagliptin, trade name OnglyzaTM) of Bristol-Myers Squibb and AstraZeneca was approved by the US Food and Drug Administration (FDA), becoming the third DPP-IV to be marketed Inhibitor type Ⅱ diabetes treatment drugs. [0003] [0004] Comprehensive analysis of the reported literature on saxagliptin concluded that the synthesis of saxagliptin has the following two important intermediates: intermediate Ⅱ-2 and intermediate Ⅱ-3: [0005] [0006] How to synthesize intermediate Ⅱ-2 and intermediate Ⅱ-3 easily and efficiently is a key factor restricting process optimization. [0007] Regarding the synthesis of compound Ⅱ-2, there are many methods reported in the literature, and the method of preparing from ketoacids has also received extensive attention because of its novelty, which can obtain amino ac...

Claims

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Application Information

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IPC IPC(8): C07C229/28C07C227/08
Inventor 刘烽潘仙华白书培赵东贤于万盛史尧陈思羽
Owner SHANGHAI INSTITUTE OF TECHNOLOGY
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