Preparation method of phenylglycine methyl ester methyl hydrogen sulfate

A technology of phenylglycine methyl ester and methyl hydrogen sulfate, applied in the field of pharmaceutical synthesis, can solve problems such as difficulty in waste gas treatment, and achieve the effects of high esterification reaction yield, reduced production cost, and high product yield

Inactive Publication Date: 2017-07-18
ZHEJIANG ANGLIKANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

CN201510249330.9 and "Zhejiang Chemical Industry" 2014 Issue 04 disclose the synthesis method of phenylglycine methyl ester hydrochloride: phenylglycine is esterified into a salt reaction in a thionyl chloride-methanol system, and there are by-products of sulfur dioxide and Hydrogen chloride is produced, which brings difficulties to waste gas treatment

Method used

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  • Preparation method of phenylglycine methyl ester methyl hydrogen sulfate
  • Preparation method of phenylglycine methyl ester methyl hydrogen sulfate
  • Preparation method of phenylglycine methyl ester methyl hydrogen sulfate

Examples

Experimental program
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Effect test

Embodiment 1

[0048] Test device: 500ml glass reaction bottle, equipped with a vacuum-insulated glass split column with a length of 150cm, an inner diameter of 2.5cm, and a built-in glass spring packing; a water distributor (water outlet from the upper end) and a glass condenser at the top of the fractionation column.

[0049]Test operation: Add 100g of L-phenylglycine and 250ml of methanol into the reaction bottle, add 80g of sulfuric acid dropwise under stirring, heat up to 70-75°C, reflux for 1 hour, cool slightly, add 100ml of dichloromethane, heat up to reflux, and reach the top temperature When the temperature is stable at 38.1-38.2°C, start to fractionate with water, the fractionated methylene chloride / water azeotrope is condensed and layered in the water separator, the water is in the upper layer, which can be separated from the upper end, and the lower layer is dichloromethane , back into the fractionation column. After refluxing with water for about 6 hours, when almost no water c...

Embodiment 2

[0060] Test device: 500ml glass reaction bottle, equipped with a vacuum-insulated glass split column with a length of 150cm, an inner diameter of 2.5cm, and a built-in glass spring packing; a water distributor (water outlet from the upper end) and a glass condenser at the top of the fractionation column.

[0061] Test operation: Add 100g of L-phenylglycine and 300ml of recovered methanol into the reaction flask, add 80g of sulfuric acid dropwise under stirring, heat up to 70-75°C, reflux for 1 hour, cool slightly, add 120ml of recovered dichloromethane, heat up to reflux, until When the top temperature is stable at 38.1-38.2°C, fractional distillation begins with water, and the dichloromethane / water azeotropic mixture obtained by fractionation is condensed and layered in the water separator. The water is in the upper layer and can be separated from the upper end, and the lower layer is two Chloromethane, back into the fractionation column. After refluxing with water for about ...

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Abstract

The invention discloses a preparation method of phenylglycine methyl ester methyl hydrogen sulfate and belongs to the technical field of chemical synthesis. The preparation method is characterized by comprising the following steps: adding phenylglycine and methanol into a reactor containing a rectifying and water separating device, and adding excessive amount of concentrated sulfuric acid, wherein the mol ratio of phenylglycine to the concentrated sulfuric acid in usage amount is 1:(1-2); then heating, refluxing, carrying out esterification reaction, then adding an azeotropic water-carrying agent dichloromethane, and continuously separating out water which is carried out by azeotrope of dichloromethane and water and is produced by the esterification reaction by virtue of the top of a rectifying tower, wherein the esterification reaction of the phenylglycine is basically complete after refluxing and water carrying are carried out for a period of time. The preparation method disclosed by the invention has the advantages of simplicity in operation, short working procedure time and high product yield.

Description

[0001] Technical field: [0002] The invention belongs to the technical field of medicine synthesis, and in particular relates to a preparation method of an intermediate phenylglycine methyl ester and a salt thereof used in the process of enzymatically synthesizing β-lactam antibiotics. [0003] Background technique: [0004] Phenylglycine methyl hydrogen sulfate methyl ester salt, its chemical structure general formula is as follows: [0005] [0006] Phenylglycine methyl hydrogen sulfate due to the difference in its three-dimensional structure, including mixed-rotary phenylglycine methyl hydrogen sulfate, L-phenylglycine methyl hydrogen sulfate and D-phenylglycine methyl hydrogen sulfate Salt. Among them, L-phenylglycine methyl hydrogen sulfate methyl ester salt is an important intermediate for the enzymatic synthesis of cephalexin, ampicillin and cefaclor. [0007] With the public's increasing attention and attention to health, environmental protection and green circula...

Claims

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Application Information

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IPC IPC(8): C07C227/18C07C229/36C07C303/24C07C305/06
CPCC07C227/18C07C303/24C07C229/36C07C305/06
Inventor 徐成苗求满金俞聚叶树祥
Owner ZHEJIANG ANGLIKANG PHARMA
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