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Synthesis method of L-serine methyl ester sulfate

A technology of serine methyl ester and synthesis method, which is applied in the field of synthesis of L-serine methyl ester sulfate, can solve the problems such as the large amount of solvent used for L-serine methyl ester sulfate, and achieves shortening production cycle, improving yield, reducing The effect of energy consumption and production cost

Pending Publication Date: 2021-06-22
淮北市博康生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved in the present invention is to overcome the large defect of L-serine methyl sulfate solvent used in the prior art, and provide a kind of synthetic method of L-serine methyl sulfate

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] A kind of synthetic method of L-serine methyl sulfate, comprises the following steps:

[0024] Initial response:

[0025] Add 200kg of L-serine and 700L of methanol into the reactor, cool down to 20°C, and slowly add 330kg of sulfuric acid dropwise; among them, the temperature of the dropping process is controlled at 20-30°C, and the dropping rate is 40kg / h; Raise the temperature to 38°C, react for 48h, and after cooling crystallization and centrifugation, vacuum-dry at 60°C for 10h to finally obtain L-serine methyl sulfate.

[0026] Using this method, 390.6 kg of white solid was obtained with a yield of 94.5% and a purity of 99.6%.

[0027] The reclaimed methanol removed in the centrifugation process is directly used as the mother liquor for the next cycle.

[0028] First time application:

[0029] Add 200kg of L-serine, 300L of methanol and 460L of recovered methanol into the reactor, lower the temperature to 20°C, and slowly add 200kg of sulfuric acid dropwise; wh...

Embodiment 2

[0046] A kind of synthetic method of L-serine methyl sulfate, comprises the following steps:

[0047] Initial response:

[0048] Add 200kg of L-serine and 600L of methanol into the reactor, cool down to 20°C, and slowly add 340kg of sulfuric acid dropwise; among them, the temperature of the dropping process is controlled at 20-30°C, and the rate of dropping is 35kg / h; Raise the temperature to 35°C, react for 36 hours, and after cooling crystallization and centrifugation, vacuum-dry at 60°C for 10 hours to finally obtain L-serine methyl sulfate. The tail gas produced during this reaction process was absorbed by KOH aqueous solution.

[0049] Using this method, 385.7 kg of white solid was obtained, with a yield of 93.4% and a purity of 99.3%.

[0050] The reclaimed methanol removed in the centrifugation process is directly used as the mother liquor for the next cycle.

[0051] First time application:

[0052] Add 200kg of L-serine, 290L of methanol and 360L of recovered meth...

Embodiment 3

[0068] A kind of synthetic method of L-serine methyl sulfate, comprises the following steps:

[0069] Initial response:

[0070] Add 200kg of L-serine and 1000L of methanol into the reactor, cool down to 20°C, and slowly add 270kg of sulfuric acid dropwise; among them, the temperature of the dropping process is controlled at 20-30°C, and the rate of dropping is 30kg / h; Raise the temperature to 40°C, react for 24 hours, and after cooling crystallization and centrifugation, vacuum-dry at 60°C for 10 hours to finally obtain L-serine methyl sulfate. The tail gas generated during this reaction process was absorbed by aqueous sodium carbonate solution.

[0071] Using this method, 381.6 kg of white solid was obtained with a yield of 92.4% and a purity of 98.7%.

[0072] The reclaimed methanol removed in the centrifugation process is directly used as the mother liquor for the next cycle.

[0073] First time application:

[0074] Add 200kg of L-serine, 300L of methanol and 760L of ...

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PUM

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Abstract

The invention discloses a synthesis method of L-serine methyl ester sulfate, which comprises the following steps: initial reaction: adding L-serine into a solvent, controlling the temperature at 20-30 DEG C, dropwise adding sulfuric acid, heating to 35-40 DEG C after dropwise adding, and reacting for 24-48 hours to obtain a reaction mixture; cooling and crystallizing the reaction mixture, centrifuging to remove the solvent, and drying to obtain L-serine methyl ester sulfate; directly using recovered methanol removed in the centrifugal desolventizing process as mother liquor of the next cycle; and performing mechanical application reaction: changing the solvent in the initial reaction into a mixture of methanol B and recovered methanol. According to the method, the mother liquor in the previous step is used as the raw material, so that the use amount of the solvent is small, and the yield of the final product is conveniently improved; the solvent can be infinitely used, no solid waste is generated, the energy consumption and the production cost are reduced, and the efficiency is improved; the product does not need to be recrystallized, so that the production period is shortened, and the yield is improved.

Description

technical field [0001] The invention relates to the technical field of preparation of ramipril intermediates, in particular to a synthesis method of L-serine methyl sulfate. Background technique [0002] Ramipril, chemical name is (S)-2-[N-(1-ethoxycarbonyl-3-phenyl-propyl)alanyl]-2-azabicyclo[3.3.0]octane -3-Carboxylic acid. Ramipril is an antihypertensive drug that has a good effect on patients with severe hypertension. [0003] L-serine methyl sulfate is a very important intermediate for the synthesis of ramipril. The preparation method of L-serine methyl ester hydrochloride in the prior art is to add L-serine into methanol, and add thionyl chloride dropwise, and then carry out a reflux reaction at 60°C. After the reaction, the reaction solution is distilled Dry, add ethanol to cool and crystallize, and centrifuge to obtain the product. However, the solvent thionyl chloride in the above scheme is highly corrosive and irritating, and can cause burns to the human body. ...

Claims

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Application Information

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IPC IPC(8): C07C227/02C07C229/22C07C227/18
CPCC07C227/02C07C227/18C07C229/22
Inventor 王金荣张小平钱国民邱永贵范昌华
Owner 淮北市博康生物科技有限公司
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