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Synthesizing method of nafcillin sodium-hydrate

A technology of nafcillin sodium monohydrate and synthesis method, which is applied in the field of medicine and can solve problems such as the instability of nafcillin sodium

Inactive Publication Date: 2010-07-21
北京紫萌医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this method is that nafcillin sodium is unstable in aqueous solution, and decompression distilled water makes nafcillin sodium be decomposed

Method used

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  • Synthesizing method of nafcillin sodium-hydrate
  • Synthesizing method of nafcillin sodium-hydrate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Add 38Kg of DMF and 18.82Kg of 2-hydroxy-1-naphthoic acid into a 200L reactor, stir to dissolve, control the temperature at 20-30°C, add 8.8Kg of sodium hydroxide, and continue stirring for 30 minutes after adding, to obtain a gray viscous liquid. Add 38.7 kg of diethyl sulfate dropwise. After the addition, a clear brown liquid was obtained. Continue stirring for 5 h. Under cooling in an ice-water bath, add 80 kg of 10% NaOH aqueous solution, stir for 30 min, and separate into layers. The aqueous layer is extracted twice with 35 kg of ether and combined. The ether layer and the oil layer were distilled off to obtain 17.1Kg of brown oil intermediate (I) ethyl 2-ethoxy-1-naphthoate.

Embodiment 2

[0017] Add 38Kg of DMF and 18.82Kg of 2-hydroxy-1-naphthoic acid into a 200L reactor, stir to dissolve, control the temperature at 20-30°C, add 8.8Kg of sodium hydroxide, and continue stirring for 30 minutes after adding, to obtain a gray viscous liquid. Add 16.2 kg of bromoethane dropwise, and after the addition, a clear brown liquid is obtained. Continue to stir for 5 h, add 80 kg of 10% NaOH aqueous solution under cooling in an ice-water bath, stir for 30 min, and separate into layers. The aqueous layer is extracted twice with 35 kg of ether, and the ether is combined. layer and oil layer, diethyl ether was distilled off to obtain 14.2Kg of brown oil intermediate (I) ethyl 2-ethoxy-1-naphthoate.

Embodiment 3

[0019] Add 17kg of intermediate (I), 15.7kg of potassium hydroxide, and 63kg of 95% ethanol in a 200L reactor, reflux for 4h, concentrate under reduced pressure to obtain a solid, add water to dissolve the solid, and wash the above solution twice with dichloromethane; Add 10% dilute hydrochloric acid to the layer dropwise to pH 2.0-3.0, stir at room temperature for 1 hour, filter, rinse the filter cake with a large amount of water until the filtrate is neutral; dry to obtain a brown powder

[0020] (II) 14.1 kg of 2-ethoxy-1-naphthoic acid.

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Abstract

The invention relates to a synthesizing method of nafcillin sodium-hydrate. 2-hydroxy-1-naphthoic acid is adopted as the initial raw material to be ethylized to obtain 2-ethyoxyl-1-ethyl naphthalene, the 2-ethyoxyl-1-ethyl naphthalene is hydrolyzed, chloridized and is coupled with 6-APA to obtain the nafcillin acid, and the nafcillin acid is salified in the mixed solution of acetone of sodium bicarbonate or sodium carbonate to directly prepare the target product nafcilin sodium-hydrate. The product prepared with the method has low cost, is easy to obtain the raw materials, has simple process, and is easy to control the residual solvent. The content is me than 99.5 percent. The product is applicable to the industrialized production.

Description

Technical field: [0001] The invention relates to a method for synthesizing nafcillin sodium monohydrate, which belongs to the technical fields of medicine and chemical industry. Background technique: [0002] Nafcillin sodium is also known as new penicillin III, new penicillin triethoxynaphthalene, new green III, chemical name (2S, 5R)-3,3-dimethyl-6-(2-ethoxy-1- Naphthyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-sodium carboxylate monohydrate, molecular formula C 21 h 21 o 5 N 2 SNa·H 2 O is developed by WYETH Company in the United States. It is characterized by acid resistance and penicillinase resistance. It can be taken orally and injected. It is mainly used for respiratory tract infections and skin infections caused by drug-resistant Staphylococcus aureus, and can also be used for osteomyelitis. [0003] There are few reports about the synthesis of nafcillin sodium, and the patent (CN 101456869A) reports the ratio of 2-ethoxyl-1-naphthoic acid: thionyl chloride: t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D499/74C07D499/16
Inventor 张伟平张靖
Owner 北京紫萌医药科技有限公司
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