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Novel process for synthesizing 3-deacetyl cefuroxime sodium (DCCF)

A technology of acetyl cefuroxime and acetyl cephalosporanic acid, which is applied in the new process field of 3-deacetyl cefuroxime acid synthesis, can solve the problems of solvent recovery difficulties, long production cycle, and many solvents, and achieve the reduction of solvent types, The effect of shortening the production cycle and reducing energy consumption

Inactive Publication Date: 2008-10-22
河源市制药工程技术研究开发中心
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] 2. Many solvents (dichloromethane, DMF, methanol) are used in the synthesis, and solvent recovery is difficult
[0008] 3, yield is lower (weight yield is 125%, and molar yield is 89.2%)
[0009] 4. Long production cycle and high energy consumption

Method used

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  • Novel process for synthesizing 3-deacetyl cefuroxime sodium (DCCF)
  • Novel process for synthesizing 3-deacetyl cefuroxime sodium (DCCF)
  • Novel process for synthesizing 3-deacetyl cefuroxime sodium (DCCF)

Examples

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Effect test

example 1

[0032] (1) Synthesis of cefuroxime side chain (SMFA acid chloride): add 4.16kg of phosphorus pentachloride (with D-7-ACA molar ratio range: 1:1) and 70L of dichloromethane into the cleaned and dried reaction tank and stir to dissolve , lower the temperature to: -15~-50°C, add 5L DMF continuously, control the feeding process for 10-15 minutes, and control the temperature not higher than -20°C, after the addition is completed, continue to add 3.72kg furan ammonium salt (with D-7- ACA molar ratio range: 1:1), control the temperature at -5°C to -25°C and stir for 90 minutes, wash with ice water three times after the reaction, and cool the organic phase to 15°C to -20°C for storage.

[0033] (2) Preparation of deacetylcefturoxime acid: Add 26L of purified water and 4.65kg of D-7-ACA to the cleaned reaction tank, cool down to 0-10°C, add NaOH solution to adjust the pH to 7.5-8.5 to dissolve, after the dissolution is complete , add the organic phase containing SMIA acid chloride prep...

example 2

[0035] (1) Synthesis of cefuroxime side chain (SMFA acid chloride): add 8.4kg phosphorus pentachloride (with D-7-ACA molar ratio: 2:1) and 70L dichloromethane into the cleaned and dried reaction tank and stir to dissolve , lower the temperature to: -15~-50°C, add 5L DMA continuously, control the feeding process for 10-15 minutes, control the temperature not higher than -20°C, after the addition is complete, continue to add 7.45kg furan ammonium salt (with D-7- The molar ratio of ACA is 2:1), and the temperature is controlled at -5°C to -25°C to stir and react for 90 minutes. After the reaction is completed, wash with ice water three times, and the organic phase is cooled to 15°C to -20°C for storage.

[0036] (2) Preparation of deacetylcefturoxime acid: Add 26L of purified water and 4.65kg of D-7-ACA to the cleaned reaction tank, cool down to 0-10°C, add NaOH solution to adjust the pH to 7.5-8.5 to dissolve, after the dissolution is complete , add the organic phase containing ...

example 3

[0038] (1) Synthesis of cefuroxime side chain (SMFA acid chloride): add 20.84kg of phosphorus pentachloride (with D-7-ACA molar ratio: 5:1) and 150L of dichloromethane into the cleaned and dried reaction tank and stir to dissolve , lower the temperature to: -15~-50°C, add 10L DMF continuously, control the feeding process for 10-15 minutes, control the temperature not higher than -20°C, after the addition, continue to add 18.6kg furan ammonium salt (with D-7- The molar ratio of ACA is 5:1), the temperature is controlled at -5°C to -25°C and the reaction is stirred for 90 minutes, after the reaction is completed, it is washed with ice water three times, and the organic phase is cooled to 15°C to -20°C and stored for later use.

[0039] (2) Preparation of deacetylcefturoxime acid: add 26L of purified water and 4.65kg of D-7-ACA to the cleaned reaction tank, cool down to 0-10°C, add NaOH solution to adjust the pH to 7.5-8.5 to dissolve, after the dissolution is complete , add the ...

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Abstract

The invention relates to a synthesis art of a chemical product, in particular to a new synthesis art for 3-deacetyl cefuroxime acid (DCCF). The art of the invention uses SMIA acyl chloride and 3-deacetyl cephalosporin acid (D-7-ACA) as the main synthesis ingredients to replace the SMIA acyl chloride and the 7-ACA, which reduces the chemical reaction process needed in the synthesis, shortens the production cycle, reduces the using solvent species, facilitates the solvent recovery and improves the product synthesis rate.

Description

Technical field: [0001] The invention relates to a synthesis process of chemical products, in particular to a new synthesis process of 3-deacetyl cefuroxime acid (DCCF). Background technique: [0002] 3-Deacetyl cefuroxime acid (chemical name: (6R,7R)-7-[2-furyl(methoxyimino)acetamido]-3-hydroxymethyl-8-oxo-5-thia -1-Azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid or (6R,7R)-7-[2-furyl(methoxyimino)acetamido]-3-hydroxymethyl - Cephalosporanic acid, also known as DCCF) is an important raw material for pharmacy. At present, the technical status of 3-deacetyl cefuroxime synthesis is as follows: [0003] (1) Preparation of SMIA acid chloride: Add 8.4kg of phosphorus pentachloride and 70L of dichloromethane into the cleaned and dried reaction tank, stir and dissolve, then cool down to -40°C, add 5L of DMA, and control the feeding process for 10-15 minutes. The temperature is not higher than -20°C. After the addition is complete, continue to add 7.5kg of furan ammonium salt, contr...

Claims

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Application Information

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IPC IPC(8): C07D501/34A61P31/04
Inventor 邓玉开潘行远杜穿
Owner 河源市制药工程技术研究开发中心
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