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(s)-3-hydroxyadamantylglycine preparation method

An adamantane glycine and hydroxygold technology, which is applied in the field of preparation of -3-hydroxyadamantane glycine, can solve the problems of low enantioselectivity, high cost of biocatalytic enzymes, unsuitable for domestic production, etc. The effect of high bioselectivity, pollution-free industrial production, and easy industrial production

Inactive Publication Date: 2015-09-09
JIAXING UNIV
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Benefits of technology

This patented technology uses two different starting materials - 3-(β)-hydoxyimidazolidone-4'-olicacylphenylacetic acid or its salt with amines that can form complexes called caged molecules containing this compound. These complexed structures are useful as an inducer for certain chemical reactions like optical resolution. By reacting these complexes with other substances at specific temperatures, it becomes possible to make highly pure products from them.

Problems solved by technology

The technical problem addressed in this patented text relates to finding an efficient way to make medicine called sarazapir® without causing unwanted side effects such as blood pressure lowering or other negative health outcomes associated with these drugs like nitroguanylin).

Method used

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  • (s)-3-hydroxyadamantylglycine preparation method
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preparation example Construction

[0021] Preparation of quinoline type alkaloid cinchonine sulfonate derivatives:

[0022] In a 250ml two-necked flask, add cinchonine (3.1g) and solvent chloroform (50ml) where R is methyl, stir to dissolve and cool to below 10°C with ice water, then slowly add chlorosulfonic acid (1.2g) in chloroform Solution, reaction control below room temperature, stirring reaction, TLC monitoring reaction is complete, add sodium bicarbonate (3g) aqueous solution, stir for 3 hours, evaporate part of solvent under reduced pressure, then add sodium bicarbonate solution and carry out liquid separation, collect water phase , part of the water was distilled off under reduced pressure, cooled and crystallized to obtain 1.3 g of the product. MS(EI): 411.14.

[0023] 1 H NMR: 1.13-1.50(2H), 1.69-1.78(3H), 2.16(1H), 2.60(1H), 2.62(1H), 3.05(1H), 3.11(1H), 3.51(1H), 3.60(3H ), 3.92(1H), 4.90(1H), 4.95(1H), 5.49(1H), 5.72(1H), 7.44(1H), 7.46(1H), 7.56(1H), 7.92(1H), 8.45(1H ).

[0024] Compounds ...

Embodiment 1

[0026] Add 2-(3-hydroxyl-1-adamantane)-2-oxoacetic acid (20.0g, 89mmol) and quinoline alkaloid cinchonine sulfonate (0.6g) successively in a 250ml two-necked flask , 60g of 5% aqueous sodium hydroxide solution and p-hydroxybenzylamine (15.4g, 0.125mol) mixture was heated up to 40°C, concentrated after 12 hours of reaction, reacted with concentrated hydrochloric acid to adjust the pH value of the reaction solution to about 6, and then frozen to -5°C The product was precipitated left and right, and 19.69 g of the product was obtained by freeze-drying after suction filtration, the ee value was 97.1%, and the yield was 98.2%.

Embodiment 2

[0028] Add 2-(3-hydroxyl-1-adamantane)-2-oxoacetic acid (20.0g, 89mmol) and quinoline alkaloid cinchonine sulfonate (0.8g ), 5% aqueous sodium hydroxide solution 80g and p-hydroxybenzylamine (15.4g, 0.125mol), the mixture was heated up to 40°C, concentrated after 12 hours of reaction, reacted with concentrated hydrochloric acid to adjust the pH value of the reaction solution to about 6 and then frozen to - The product was precipitated at about 5°C, and 19.4 g of the product was obtained by freeze-drying after suction filtration, with an ee value of 98.5% and a yield of 96.8%.

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Abstract

The invention relates to a (s)-3-hydroxyadamantylglycine preparation method, which takes 2-(3-hydroxy-1-adamantane)-2-glyoxalic acid as a raw material, in a sodium hydroxide aqueous solution, under effects of a chiral catalyst and p-hydroxybenzylamine, (s)-3-hydroxyadamantylglycine can be generated, wherein the chiral catalyst is a quinoline alkaloid cinchonine derivative. The preparation method has the characteristics of mild reaction condition, high product yield, high purity and high enantiomer selectivity, has the advantages of short route, simple operation, no pollution and easy industrial production, and is the economic and simple method.

Description

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Claims

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Application Information

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Owner JIAXING UNIV
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