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 effect of short cycle, easy operation and mild reaction conditions

Inactive Publication Date: 2012-05-30
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The purpose of the present invention is to propose a preparation method for 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
  • Preparation method of L-erythro biopterin

Examples

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Embodiment 1

[0039] The preparation method of L-erythrotype biopterin, its specific preparation steps are as follows:

[0040] 1) Dissolve 10g of L-(+)-arabinose 1 in 20mL of concentrated hydrochloric acid, stir, then add 18mL of n-dodecyl mercaptan, stir, acetal reaction occurs, and the reaction time is 18 hours; extracting, drying the extract with magnesium sulfate, and filtering to remove the magnesium sulfate after drying to obtain a filtrate;

[0041] 2) Cool the filtrate obtained in step 1) to 0°C, then add 10mL triethylamine, then add 12.6g p-toluenesulfonyl chloride, stir, and the reaction time is 24 hours; after the reaction is completed, use saturated aqueous sodium bicarbonate Washing three times, separating the layers, drying the organic phase with magnesium sulfate, filtering, and then distilling off the solvent under reduced pressure to obtain the product 3';

[0042] 3) Dissolve the product 3' obtained in step 2) in 200 mL of tetrahydrofuran, cool to 0° C., then add 2.2 g o...

Embodiment 2

[0055] The preparation method of L-erythrotype biopterin, its specific preparation steps are as follows:

[0056] 1) Dissolve 10g of L-(+)-arabinose 1 in 20mL of concentrated hydrochloric acid, stir, then add 18mL of n-dodecyl mercaptan, stir, acetal reaction occurs, and the reaction time is 18 hours; extracting, drying the extract with magnesium sulfate, and filtering to remove the magnesium sulfate after drying to obtain a filtrate;

[0057] 2) Cool the filtrate obtained in step 1) to 0°C, then add 10mL triethylamine, then add 12.6g p-toluenesulfonyl chloride, stir, and the reaction time is 24 hours; after the reaction is completed, use saturated aqueous sodium bicarbonate Washing three times, separating the layers, drying the organic phase with magnesium sulfate, filtering, and then distilling off the solvent under reduced pressure to obtain the product 3';

[0058] 3) Dissolve the product 3' obtained in step 2) in 200mL DMSO, cool to 0°C, then add 2.2g sodium borohydride,...

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Abstract

The invention relates to a preparation method of L-erythro biopterin used as a 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 alkyl hydrosulfide by acetalization; adding sulfonyl chloride for generating a sulfonation reaction; reducing and removing sulfonyl ester; removing reduced sulfur 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 the L-erythro biopterin. The invention ensures deodorizing equipment is not installed on a reaction system by utilizing Odourless mercaptan, thereby saving costand optimizing a working environment; and the invention has mild reaction condition of each step, short period and easy operation.

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 ( BH4) is an essential coenzyme in hydroxylation reaction and oxygenase in organisms, and is the most important coenzyme of nitric oxide synthase (NOS); sapropterate hydrochloride is a drug approved by many...

Claims

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Application Information

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Patent Type & Authority Patents(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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