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Method for synthesizing vitamin K2

A synthetic method and technology of vitamins, applied in chemical instruments and methods, preparation of organic compounds, metal/metal oxide/metal hydroxide catalysts, etc., can solve problems such as complex processes, adverse effects on product quality and yield, Achieve the effect of good product purity, beneficial to industrial production and high yield

Inactive Publication Date: 2008-03-12
NAN JING RHINE PHARM TECH
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  • Abstract
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  • Claims
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AI Technical Summary

Problems solved by technology

[0004] Among the many vitamin K 2 In the synthesis research, there are 2-bromo-3-methyl-1,4-dimethoxynaphthalene main ring, carry out Grignard reaction and polyprenyl coupling (①SynderC D, J.Am.Chem.Soc ., 13(7):8046-8054, 1974; ②Chanard B L, J.Org.Chem, 45(3):378-384, 1980; ③Syper L.Tetrahedron, 36(1):123-129, 1979) among them The intermediate 2-bromo-3-methyl-1,4-methoxynaphthalene is based on 2-methylnaphthoquinone, which undergoes bromination, reduction, and methoxylation, resulting in a coupling side chain , but one more demethylation reaction will have an adverse effect on product quality and yield
[0005] In 1994, Hamamura et al. (U.S.Pat 5,412,124; 5,476,995); proposed a method for the addition of menadione-cyclopentadiene to synthesize vitamins. The yield is high, but the process is still relatively complicated, and it needs to go through D-A addition and reverse D-A reaction

Method used

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  • Method for synthesizing vitamin K2
  • Method for synthesizing vitamin K2

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Embodiment one, vitamin K 2(10) preparation of

[0023] In a 1000ml three-necked flask, put 600ml of anhydrous tetrahydrofuran as a solvent, fill with nitrogen, put in 86.8 (0.4mol) of geranyl bromide, 25.6g (0.4mol) of zinc powder, and finally put in vitamin K 3 68.8g (0.4mol), heated to reflux for 6 hours while stirring, distilled off tetrahydrofuran under reduced pressure, added 400ml of hexane, and filtered off the insoluble matter in hexane. Then the hexane solution was concentrated, and the residual oil was chromatographed on silica gel, eluted with hexane:ethanol=1:1 solution, and VK was isolated 2 (10) 91.8g, yield 74.5%, purity (HPLC): 98.6%. Confirm no VK 3 Check out.

Embodiment 2

[0024] Embodiment two, vitamin VK 2(20) preparation of

[0025] Put 400ml of anhydrous tetrahydrofuran into a 1000ml three-necked flask, add 12.8g (0.2m) of zinc powder, 124.0g (0.2ml) of geranylgeranyl bromide, fill with nitrogen, and add vitamin K as soon as possible 3 34.4g (0.2mol), heated to reflux for 5 hours while stirring, and the reaction was completed. Evaporate tetrahydrofuran under reduced pressure, add hexane to filter to remove insoluble matter, concentrate the hexane solution, and subject the oil to silica gel column chromatography, eluting with ethanol: hexane = 1: 1 to obtain Vitamin K 2(20) 52.3g, yield 58.8g%, purity (HPLC): 98.2%, confirmed no VK 3 Check out.

Embodiment 3

[0026] Embodiment three, vitamin K 2(45) preparation of

[0027] In a 1000ml three-necked flask, put 400ml of anhydrous isopropyl ether, add tin powder 35.8g (0.2mol), and solanyl bromide 139.0g (0.2mol), fill with nitrogen, and add VK as soon as possible 3 34.4g (0.2mol), heated to reflux for 6 hours, the reaction was completed, distilled off isopropyl ether under reduced pressure, added hexane, filtered to remove insoluble matter, concentrated hexane solution, the oil was subjected to silica gel column chromatography, and ethanol: hexane Alkane = 1:1 elution to get vitamin K 2(45) 88.7g, yield 56.6g%, purity (HPLC): 98.3%, VK 3 ≤0.5%.

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Abstract

The present invention provides a synthesis method of the vitamin K 2 represented by the vitamin K2(10), K2(20) and K2(45). Specifically the present invention is a synthesis method of the vitamin K 2 , which is characterized in the condensation reaction of the vitamin K3 and the halide of the plant alcohol with the influence of the transition metal elements.

Description

field of invention [0001] The present invention relates to the field of organic medicinal chemistry, in particular, the present invention relates to vitamin K 2 synthetic method. Background technique [0002] Vitamin K (Vitamin K) also known as blood coagulation vitamin, vitamin K 2 It is an essential substance for the formation of blood coagulation in the liver. Vitamin K 2 It is mainly used to treat gastrointestinal bleeding and intracranial hemorrhage in neonatal period and infants, and prevent liver cirrhosis from progressing to liver cancer (JAMA, 292:358-361, 2004). Vitamin K 2 More and more people pay more and more attention to the role of this compound, which exists in nature and can also be synthesized artificially. [0003] In 1958, Isler et al. (Helv. Chim. Acta 41, 786, 1958) first chemically synthesized vitamin K 2 series. [0004] Among the many vitamin K 2 In the synthesis research, there are 2-bromo-3-methyl-1,4-dimethoxynaphthalene main ring, carry ou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C50/14C07C46/00B01J23/70B01J23/06B01J23/14
CPCC07C46/00C07C50/14
Inventor 陈新徐承石
Owner NAN JING RHINE PHARM TECH
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