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Method for preparing valienamine

A technology of Jinggangmemamine and metal, applied in the field of preparation of Jinggangmemamine, can solve problems such as being too complicated and unable to be used for mass production and the like

Inactive Publication Date: 2007-10-03
CHEMTECH RESEARCH INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this overall synthetic method is too complicated because the synthesis reaction requires at least 10 reaction steps, and thus cannot be adopted for mass production

Method used

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  • Method for preparing valienamine
  • Method for preparing valienamine
  • Method for preparing valienamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1: Jinggang mycylamine is prepared by acarbose (1)

[0036] Acarbose (10 g) and sodium hydroxide (9.3 g) were added to water (200 mL), followed by reflux for 48 hours. The reaction mixture was cooled to room temperature, neutralized with 1N hydrochloric acid solution, and then concentrated. The concentrated reaction mixture was purified with cation exchange resin (Amberlite IR-120H) and weak acid cation exchange resin (Amberlite CG-50). As a result, pure mycoenamine (1.1 g) was obtained.

[0037] The hydrogen NMR spectrum of the product (Jinggang mycylamine) formed is as follows:

[0038] 1 H NMR (D 2 O, 300MHz) 3.35(m, 1H), 3.49(m, 2H), 3.80-3.95(m, 2H), 4.02(d, 1H), 5.61(d, 1H)

Embodiment 2

[0039] Embodiment 2: Preparation of Jinggang mycylamine by acarbose (2)

[0040] Acarbose (10 g) and potassium hydroxide (10.5 g) were added to water (180 mL), followed by reflux for 48 hours. The reaction mixture was cooled to room temperature, neutralized with 1N hydrochloric acid solution, and then concentrated. The concentrated reaction mixture was purified with cation exchange resin (Amberlite IR-120H) and weak acid cation exchange resin (Amberlite CG-50). As a result, pure mycoenamine (1.0 g) was obtained.

Embodiment 3

[0041] Embodiment 3: Jinggang mycylamine is prepared by acarbose (3)

[0042]Acarbose (1.0 g) and calcium hydroxide (1.6 g) were added to water (20 mL), followed by reflux for 60 hours. The reaction mixture was cooled to room temperature, then concentrated. The concentrated reaction mixture was purified with cation exchange resin (Amberlite IR-120H) and weak acid cation exchange resin (Amberlite CG-50). As a result, pure mycoenamine (0.12 g) was obtained.

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Abstract

The present invention provides a method for preparing valienamine from acarbose or acarbose derivatives by using a base. The present invention provides an improved method for preparing valienamine compared to conventional preparation methods of valienamine by simplifying the reaction steps and diminishing byproducts.

Description

technical field [0001] The present invention relates to the preparation method of valienamine represented by the following structural formula (1). More specifically, the present invention relates to a method for preparing mycamine from acarbose or acarbose derivatives by using a base. [0002] Background technique [0003] Jinggang mycetamine is the core precursor for the preparation of voglibose, which is an effective hypoglycemic drug for treating diabetes and inhibiting the sudden increase in blood sugar levels after meals [Carbohydrate Research, 140, 185( 1985); J. Med. Chem., 29, 1038 (1988); US Patent 4,701,559 (1987)]. [0004] Conventional methods for synthesizing mycamine are divided into two categories. The first type synthesizes myramine from carbohydrates as a whole, and the second type prepares myramine from validamycin or acarbose which has a part of myramine. Contents of the invention [0005] technical problem [0006] In the general synthesis of jin...

Claims

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Application Information

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IPC IPC(8): C07C213/08
CPCE04H12/2215E04H12/2269E04H17/22E04H17/268
Inventor 边一锡金周晟申晟譓金完柱
Owner CHEMTECH RESEARCH INC
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