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Method for preparing nafcillin acid

A technology of nafcillin acid and ethoxy naphthoic acid, which is applied in the field of semi-synthetic extraction of antibiotic nafcillin sodium, can solve problems such as complex process, achieve the effect of reducing the degree of decomposition and increasing the yield

Inactive Publication Date: 2013-02-13
GUILIN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the method described in this invention needs to be converted into nafcillin acid after obtaining the nafcillin sodium crude product, and then carry out steps such as sodium salt formation to obtain the final nafcillin sodium product, and the process is still relatively complicated

Method used

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  • Method for preparing nafcillin acid

Examples

Experimental program
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Effect test

Embodiment 1

[0021] 1) Put 75 kg (630 mol) of thionyl chloride into a reaction tank, add 27 kg (125 mol) of 2-ethoxynaphthoic acid under stirring conditions, heat to 85° C. for reflux reaction for 3 hours, and distill off thionyl chloride under reduced pressure. The residue was dissolved with 100L of dichloromethane to obtain solution A;

[0022] 2) Put 27kg (125mol) of 6-APA, 25kg (247mol) of triethylamine and 100L of dichloromethane into another reaction tank, stir until the solution is clear, and obtain solution B;

[0023] 3) Under the condition of 10°C, add solution A obtained in step 1) dropwise to solution B to carry out condensation reaction, after the dropwise addition, keep warm for 60 minutes to obtain solution C;

[0024] 4) Add sodium acetate aqueous solution (made up of 30kg (366mol) sodium acetate and 100L water) to solution C to obtain solution D;

[0025] 5) Solution D was acidified to pH=1.5 with 4mol / L hydrochloric acid at 10°C, the organic layer was separated, washed w...

Embodiment 2

[0033] 1) Put 75 kg (630 mol) of thionyl chloride into a reaction tank, add 27 kg (125 mol) of 2-ethoxynaphthoic acid under stirring conditions, heat to 85° C. for reflux reaction for 3 hours, and distill off thionyl chloride under reduced pressure. The residue was dissolved with 100L of dichloromethane to obtain solution A;

[0034] 2) Put 27kg (125mol) of 6-APA, 25kg (247mol) of triethylamine and 100L of dichloromethane into another reaction tank, stir until the solution is clear, and obtain solution B;

[0035] 3) Under the condition of 10°C, add solution A obtained in step 1) dropwise to solution B to carry out condensation reaction, after the dropwise addition, keep warm for 60 minutes to obtain solution C;

[0036] 4) Add sodium acetate aqueous solution (made up of 30kg (366mol) sodium acetate and 100L water) to solution C to obtain solution D;

[0037] 5) Solution D was acidified with 4mol / L phosphoric acid at pH=1.5 at 10°C, the organic layer was separated, washed wit...

Embodiment 3

[0044]1) Put 75 kg (630 mol) of thionyl chloride into a reaction tank, add 27 kg (125 mol) of 2-ethoxynaphthoic acid under stirring conditions, heat to 85° C. for reflux reaction for 3 hours, and distill off thionyl chloride under reduced pressure. The residue was dissolved with 100L of dichloromethane to obtain solution A;

[0045] 2) Put 27kg (125mol) of 6-APA, 25kg (247mol) of triethylamine and 100L of dichloromethane into another reaction tank, stir until the solution is clear, and obtain solution B;

[0046] 3) Under the condition of 10°C, add solution A obtained in step 1) dropwise to solution B to carry out condensation reaction, after the dropwise addition, keep warm for 60 minutes to obtain solution C;

[0047] 4) Add sodium citrate aqueous solution (made up of 96kg (372mol) sodium citrate and 100L water) to solution C to obtain solution D;

[0048] 5) Solution D was acidified to pH = 3 with 10% mass concentration of acetic acid at 10°C, the organic layer was separat...

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Abstract

The invention discloses a method for preparing nafcillin acid. The method includes the following steps: 1) performing chlorination on 2-ethyoxyl naphthoic acid and excessive thionyl chloride to obtain acyl chloride liquid, steaming in a decompression mode to remove thionyl chloride, and dissolving the residue through dichloromethane to obtain solution A; 2) adding triethylamine and dichloromethane in 6-aminopenicillanic acid, and stirring until the solution is clear to obtain solution B; 3) dropwise adding the solution A into the solution B to perform condensation reaction, and preserving the temperature for 30-90mins to react after the dropwise adding is finished to obtain solution C; 4) adding buffer agent into the solution C to obtain solution D; and 5) acidizing the solution D to separate an organic layer, washing, drying, steaming in a decompression mode to remove dichloromethane, and performing recrystallization on the obtained solid through alcohols solvents to obtain the nafcillin acid. The method for preparing the nafcillin acid is easy and simple to operate, simple in aftertreatment and high in yield.

Description

technical field [0001] The invention relates to a semi-synthetic antibiotic nafcillin sodium, in particular to a preparation method of a nafcillin sodium intermediate nafcillin acid. Background technique [0002] Nafcillin acid is a key intermediate for the preparation of the third generation penicillin nafcillin sodium, and plays an important role in the synthesis of high-quality nafcillin sodium. The existing literature about the preparation and synthesis method of nafcillin acid is less, wherein the nafcillin acid synthesis method as reported by SIDNET S.WALKENSTEIN (J.Pharm.Sci.1963,52(8):763) is to combine 2- Ethoxyl-1-naphthoic acid, thionyl chloride and dimethylamide carry out acid chloride reaction in dichloromethane, the molar ratio of the three is 1:1.41:0.07, after the reaction finishes, react with 6-aminopenicillium Alkanoic acid (6-APA) was subjected to a comprehensive reaction at a low temperature below 10°C for 1.5 hours to prepare nafcillin acid with a yield...

Claims

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Application Information

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IPC IPC(8): C07D499/74C07D499/12
Inventor 苏钦璐潘梅陈萍
Owner GUILIN PHARMA
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