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Preparation method of L-erythro biopterin

A technology of biopterin and erythrotype, which is applied in the field of preparation of L-erythrotype biopterin, can solve the problems of strong odor and long reaction cycle, and achieve the effects of easy operation, shortened production cycle and mild reaction conditions

Inactive Publication Date: 2010-08-04
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The purpose of the present invention is to propose an effective new method for preparing L-erythro-biopterin in order to solve the problems of large odor and long reaction period in the process of preparing L-erythro-biopterin in the prior art

Method used

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  • Preparation method of L-erythro biopterin

Examples

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Embodiment 1

[0038] The preparation method of L-erythrotype biopterin, its specific preparation steps are as follows:

[0039] 1) Dissolve 10g of L-(+)-arabinose 1 in 200mL of methanol, add 2mL of 1mol / L HCl methanol solution, react at room temperature for 3 hours, add 15g of K 2 CO 3 , stirred for 30 minutes, and filtered to remove the insoluble matter; the solvent was removed under reduced pressure to obtain a viscous liquid;

[0040] 2) Mix the product obtained in step 1) with tetrahydrofuran, cool to 0°C, then add 10 mL of triethylamine, then add 12.6 g of p-toluenesulfonyl chloride, stir, and the reaction time is 24 hours; after the reaction is completed, add 10 mL of Saturated aqueous sodium bicarbonate solution, then distilled off the solvent under reduced pressure, extracted with dichloromethane, dried the organic phase with magnesium sulfate, filtered, then distilled off the solvent under reduced pressure to obtain the product 3';

[0041] 3) Dissolve the product 3' obtained in ...

Embodiment 2

[0054] The preparation method of L-erythrotype biopterin, its specific preparation steps are as follows:

[0055] 1) Dissolve 10g of L-(+)-arabinose 1 in 200mL of methanol, add 2mL of 1mol / L HCl methanol solution, react at room temperature for 3 hours, add 15mL of Et 3 N, stirred for 30 minutes, filtered to remove insoluble matter; decompressed to remove solvent to obtain viscous liquid;

[0056] 2) Cool the filtrate obtained in step 1) to 0°C, then add 10 mL of triethylamine, then add 6.0 mL of methanesulfonyl chloride, stir, and the reaction time is 24 hours; after the reaction is completed, wash with saturated aqueous sodium bicarbonate three times , layered, the organic phase was dried with magnesium sulfate, filtered, and then the solvent was distilled off under reduced pressure to obtain the product 3";

[0057] 3) Dissolve the product 3” obtained in step 2) in 200mL DMSO, cool to 0°C, then add 2.2g sodium borohydride, gradually warm up to room temperature, react for 18...

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Abstract

The invention relates to a preparation method of L-erythro biopterin used as an import preparation intermediate body of a clinically used medicament (R)-2-amido-6-[(1R,2S)-1,2-dihydroxy propyl]-5,6,7,8-tetrahydro-4(3H)-pteridine ketone hydrochloride for treating atypical hyperphenylalaninemia, which belongs to the technical field of medicinal chemistry. The preparation method sequentially comprises the steps of: reacting L-(+)-arabinose 1 with alcohol by glycosidation; adding sulfonyl chloride for generating a sulfonation reaction; reducing and removing sulfonyl ester; removing reduced aldehyde protective groups; reacting with hydrazine for obtaining a hydrazine compound; reacting with estolide or the sulfonyl chloride; reacting with 2,4,5-3-amino-pyrimidine ketone; adding an oxidant; and removing acyl for obtaining L-erythro biopterin. The invention ensures deodorizing equipment is not installed on a reaction system by utilizing Odourless mercaptan thereby reducing production cost and optimizing a working environment; and the invention has mild reaction condition of each step and easy operation, and shortens a production period.

Description

technical field [0001] The invention relates to a preparation method of L-erythrobiopterin, which is used as a clinically used therapeutic drug for atypical hyperphenylalaninemia (R)-2-amino-6-[(1R,2S)-1,2 -dihydroxypropyl]-5,6,7,8-tetrahydro-4(3H)-pteridone hydrochloride (common name: Sapropterin hydrochloride (Sapropterin hydrochloride)) preparation intermediate L-erythro The invention discloses a method for preparing type biopterin, which belongs to the technical field of medicinal chemistry. Background technique [0002] [0003] Chemical formula I represents that L-erythro-biopterin is a kind of pteridines widely existing in nature. [0004] [0005] Chemical formula II represents (R)-2-amino-6-[(1R, 2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-4(3H)-pteridone ( BH 4 ) is an essential coenzyme in the hydroxylation reaction and oxygenase in the organism, and is the most important coenzyme of nitric oxide synthase (NOS); sapropterate hydrochloride is a drug approv...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D475/04
CPCY02P20/55
Inventor 武钦佩张青山李云政席小东
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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