CN110156846A - A kind of preparation process of D-galactosamine hydrochloride - Google Patents
A kind of preparation process of D-galactosamine hydrochloride Download PDFInfo
- Publication number
- CN110156846A CN110156846A CN201910516839.3A CN201910516839A CN110156846A CN 110156846 A CN110156846 A CN 110156846A CN 201910516839 A CN201910516839 A CN 201910516839A CN 110156846 A CN110156846 A CN 110156846A
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- China
- Prior art keywords
- organic amine
- hydrochloride
- preparation process
- galactosamine
- added
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0239—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
- C07H5/06—Aminosugars
Abstract
The invention discloses a kind of preparation processes of D-galactosamine hydrochloride, are related to the technical field of anti-hepatopathy class medicine intermediate, it is intended to solve in the prior art, the problem of weight yield of D-galactosamine hydrochloride is only 25%, low output.Its key points of the technical solution are that by 5-methyltryptamine hydrochloride salt in dimethylformamide, organic amine solid-carried catalyst and chloropropene is added, it is reacted 5-6 hours under room temperature, after the filtrate that reaction solution is obtained by filtration is evaporated, it is dissolved with isopropanol, be added 34wt% hydrochloric acid carry out it is acidified to get arrive target product；The preparation of the organic amine solid-carried catalyst includes the following steps: organic amine, immobilized is added in dehydrated alcohol, after reflux, cooling, filtering, drying, as organic amine solid-carried catalyst, the organic amine are ten tetracosyl amine of dimethyl, and the immobilized phase is silica.Invention achieves the effects for improving D-galactosamine hydrochloride production yields.
Description
Technical field
The present invention relates to the technical fields of anti-hepatopathy class medicine intermediate, more particularly, to a kind of D-galactosamine hydrochloride
Preparation process.
Background technique
D-galactosamine hydrochloride is liver cell nucleoside metabolism agent interfering, can routinely damage liver cell, be mainly used for
Hepatic pathology, biochemical research, with the hepatitis model that it is replicated, close to the pathological change of human body hepatitis, for screening and studying
Antihepatitis medicament is more reliable and useful.
The Chinese patent of existing Publication No. CN1036386A discloses a kind of preparation side of D-Gal hydrochloride
Method is raw material with chondroitin sulfate, prepares D-Gal hydrochloride through hydrochloric acid hydrolysis, it is characterised in that chondroitin sulfate
Crude product need not pre-process, and directly be hydrolyzed with hydrochloric acid, through strong acid cation exchange resin column separating-purifying after hydrolysis, in ethyl alcohol second
D-Gal hydrochloride is made in crystallization in ether mixed liquor.
Prior art among the above has the following deficiencies: that above-mentioned preparation method obtains D-Gal hydrochloride,
Weight yield is only 25%, and yield is lower, low output, which has to be solved.
Summary of the invention
The object of the present invention is to provide a kind of preparation processes of D-galactosamine hydrochloride, have the effect for improving yield
Fruit.
Foregoing invention purpose of the invention has the technical scheme that
A kind of preparation process of D-galactosamine hydrochloride, which comprises the steps of: by 5-methyltryptamine hydrochloride
It is dissolved in dimethylformamide, organic amine solid-carried catalyst and chloropropene is added, is reacted 5-6 hours under room temperature, reaction solution mistake
Filter after obtained filtrate is evaporated, dissolved with isopropanol, be added 34wt% hydrochloric acid carry out it is acidified to get to target product；
The preparation of the organic amine solid-carried catalyst include the following steps: by organic amine, it is immobilized be added in dehydrated alcohol, return
After stream, cooling, filtering, drying, as organic amine solid-carried catalyst, the organic amine are ten tetracosyl amine of dimethyl, institute
Stating immobilized phase is silica.
The present invention is further arranged to: the mass volume ratio of the 5-methyltryptamine hydrochloride and dimethylformamide is 1:
2.0-3.5, g/ml.
The present invention is further arranged to: the molar ratio of the 5-methyltryptamine hydrochloride and chloropropene is 1:2.0-2.3.
The present invention is further arranged to: the mass volume ratio of the 5-methyltryptamine hydrochloride and isopropanol is 1:5-7, g/
ml。
The present invention is further arranged to: the molar ratio of the 5-methyltryptamine hydrochloride and hydrochloric acid is 1:0.9-1.0.
The present invention is further arranged to: the 5-methyltryptamine hydrochloride is 1 with organic amine solid-carried catalyst mass ratio:
0.2-0.5。
The present invention is further arranged to: the organic amine, immobilized phase and dehydrated alcohol mixture under conditions of 110 DEG C
Reflux 5-6 hours.
The present invention is further arranged to: being cooled to 25 after the organic amine, immobilized phase and the mixture reflux of dehydrated alcohol
℃-34℃。
In conclusion advantageous effects of the invention are as follows:
1. method of the invention obtains D-galactosamine hydrochloride, stable product quality is suitable for scale continuous production；
2. the present invention uses organic amine solid-carried catalyst, reaction process is effectively increased, it is cumbersome to solve post-reaction treatment
Problem.
Specific embodiment
Embodiment one
The invention discloses a kind of preparation processes of D-galactosamine hydrochloride, are having reflux condensing tube, blender and temperature
500ml dehydrated alcohol is added in the three-necked flask of the 1000ml of meter, is stirred at room temperature and is separately added into 100g dimethyl 12
The immobilized phase oxidation silicon of tetradecylamine, 500g, is warming up to 110 DEG C in 30 minutes, be down to 29 DEG C after maintaining the reflux for reaction 5 hours,
It filtered, dried, obtain 589g organic amine solid-carried catalyst.
With blender, thermometer 1000ml three-necked flask in be separately added into 190g5- methyl tryptophan hydrochloride,
59g organic amine solid-carried catalyst and 150g chloropropene is added in 600ml dimethylformamide, reacts eight hours under room temperature, reaction
Liquid filtering, is dissolved after obtained filtrate is evaporated with 1150ml isopropanol, and addition 89ml 36wt% hydrochloric acid progress is acidified, is obtained
D-galactosamine hydrochloride salt as white crystal 130.32g, yield 42.05%.
Embodiment two
The invention discloses a kind of preparation processes of D-galactosamine hydrochloride, are having reflux condensing tube, blender and temperature
500ml dehydrated alcohol is added in the three-necked flask of the 1000ml of meter, is stirred at room temperature and is separately added into 100g dimethyl 12
The immobilized phase oxidation silicon of tetradecylamine, 500g, is warming up to 110 DEG C in 30 minutes, be down to 29 DEG C after maintaining the reflux for reaction 5 hours,
It filtered, dried, obtain 589g organic amine solid-carried catalyst.
With blender, thermometer 1000ml three-necked flask in be separately added into 190g5- methyl tryptophan hydrochloride,
104g organic amine solid-carried catalyst and 200g chloropropene is added in 800ml dimethylformamide, under room temperature reaction six hours, instead
It answers liquid to filter, is dissolved after obtained filtrate is evaporated with 1654ml isopropanol, addition 100ml 36wt% hydrochloric acid progress is acidified,
Obtain D-galactosamine hydrochloride salt as white crystal 141.05g, yield 45.91%.
The embodiment of present embodiment is presently preferred embodiments of the present invention, not limits protection of the invention according to this
Range, therefore: the equivalence changes that all structures under this invention, shape, principle are done, should all be covered by protection scope of the present invention it
It is interior.
Claims (8)
1. a kind of preparation process of D-galactosamine hydrochloride, which comprises the steps of: by 5-methyltryptamine hydrochloric acid
Salt is dissolved in dimethylformamide, and organic amine solid-carried catalyst and chloropropene is added, reacts 5-6 hours under room temperature, reaction solution
After the filtrate being obtained by filtration is evaporated, dissolved with isopropanol, be added 34wt% hydrochloric acid carry out it is acidified to get to target product；
The preparation of the organic amine solid-carried catalyst include the following steps: by organic amine, it is immobilized be added in dehydrated alcohol, return
After stream, cooling, filtering, drying, as organic amine solid-carried catalyst, the organic amine are ten tetracosyl amine of dimethyl, institute
Stating immobilized phase is silica.
2. a kind of preparation process of D-galactosamine hydrochloride according to claim 1, it is characterised in that: the 5- methyl
The mass volume ratio of tryptamine hydrochloride and dimethylformamide is 1:2.5-4.0, g/ml.
3. a kind of preparation process of D-galactosamine hydrochloride according to claim 2, it is characterised in that: the 5- methyl
The molar ratio of tryptamine hydrochloride and chloropropene is 1:2.0-2.3.
4. a kind of preparation process of D-galactosamine hydrochloride according to claim 3, it is characterised in that: the 5- methyl
The mass volume ratio of tryptamine hydrochloride and isopropanol is 1:6-8, g/ml.
5. a kind of preparation process of D-galactosamine hydrochloride according to claim 4, it is characterised in that: the 5- methyl
The molar ratio of tryptamine hydrochloride and hydrochloric acid is 1:0.9-1.0.
6. a kind of preparation process of D-galactosamine hydrochloride according to claim 5, it is characterised in that: the 5- methyl
Tryptamine hydrochloride and organic amine solid-carried catalyst mass ratio are 1:0.2-0.5.
7. a kind of preparation process of D-galactosamine hydrochloride according to claim 1, it is characterised in that: described organic
Amine, immobilized phase and the mixture of dehydrated alcohol flow back 5-6 hours under conditions of 110 DEG C.
8. a kind of preparation process of D-galactosamine hydrochloride according to claim 2, it is characterised in that: described organic
25 DEG C -34 DEG C are cooled to after amine, immobilized phase and the mixture reflux of dehydrated alcohol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910516839.3A CN110156846A (en) | 2019-06-14 | 2019-06-14 | A kind of preparation process of D-galactosamine hydrochloride |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201910516839.3A CN110156846A (en) | 2019-06-14 | 2019-06-14 | A kind of preparation process of D-galactosamine hydrochloride |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1036386A (en) * | 1988-04-07 | 1989-10-18 | 张锦 | The preparation method of D-Gal hydrochloride |
| CN101432318A (en) * | 2006-03-10 | 2009-05-13 | 华威效应聚合物有限公司 | Polymers |
| CN102391170A (en) * | 2011-10-17 | 2012-03-28 | 上海化学试剂研究所 | Method for preparing N,N-diallyl-5-methoxytryptamine hydrochlorides |
-
2019
- 2019-06-14 CN CN201910516839.3A patent/CN110156846A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1036386A (en) * | 1988-04-07 | 1989-10-18 | 张锦 | The preparation method of D-Gal hydrochloride |
| CN101432318A (en) * | 2006-03-10 | 2009-05-13 | 华威效应聚合物有限公司 | Polymers |
| CN102391170A (en) * | 2011-10-17 | 2012-03-28 | 上海化学试剂研究所 | Method for preparing N,N-diallyl-5-methoxytryptamine hydrochlorides |
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Application publication date: 20190823 |