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Synthetic method of latamoxef intermediate

A synthetic method, the technology of Latamoxef, which is applied in the field of synthesis of Latamoxef intermediates, can solve the problems of low yield, achieve the effects of reducing production costs, simplifying post-treatment procedures, and reducing the production of sulfur dioxide

Inactive Publication Date: 2021-02-02
YIYUAN XINQUAN CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] (3) adopt methanol crystallization, yield is lower

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] ① Add 370g of isobutanol to the three-necked flask, check that the solvent moisture is 0.05%, add 50g of 3,3-dimethyl-6-(4-methyl-benzamido)-4,7-dioxo-4 - benzhydryl thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate.

[0033] ②Stir and heat up to 50°C, and add 17g of triethyl phosphite.

[0034] ③Heating and reflux reaction, and the by-product water is separated under a slight negative pressure (-0.005MPa).

[0035] ④ It is detected that the residual raw material is 0.9%, and the isobutanol is distilled off after the reaction is completed.

[0036] ⑤ Add 200 g of acetone to the reaction liquid after steaming the isobutanol, control the temperature at 40° C., and grow the crystal for 4 hours.

[0037] ⑥ After the crystal growth is completed, cool down to 5°C, filter with suction, and wash the material with 65g of acetone.

[0038] ⑦The product (II) was obtained after vacuum drying at 35°C for 7 hours, with a molar yield of 78.12% and a purity of 98.85%.

[0039] ⑧Steam ...

Embodiment 2

[0041] ① Add 375g of isobutanol to the three-necked flask, check the solvent moisture to 0.06%, add 50g of 3,3-dimethyl-6-(4-methyl-benzamido)-4,7-dioxo-4 - benzhydryl thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate.

[0042] ②Stir and heat up to 47°C, and add 17.5g of triethyl phosphite.

[0043] ③Heating and reflux reaction, and the by-product water is separated out under a slight negative pressure (-0.008MPa).

[0044] ④ It is detected that the residual raw material is 0.85%. After the reaction is completed, the isobutanol is distilled off.

[0045] ⑤ Add 203 g of acetone to the reaction liquid after steaming the isobutanol, control the temperature at 35° C., and grow the crystal for 3 hours.

[0046] ⑥ After the crystal growth is completed, cool down to 2°C, filter with suction, and wash the material with 70g of acetone.

[0047] ⑦The product (II) was obtained after vacuum drying at 38°C for 6.5 hours, with a molar yield of 78.04% and a purity of 98.91%.

[0048] ⑧Steam...

Embodiment 3

[0050] ① Add 370g of isobutanol to the three-necked flask, check that the solvent moisture is 0.08%, add 50g of 3,3-dimethyl-6-(4-methyl-benzamido)-4,7-dioxo-4 - benzhydryl thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate.

[0051] ②Stir and heat up to 45°C, and add 17.5g of triethyl phosphite.

[0052] ③Heating and reflux reaction, and the by-product water is separated under a slight negative pressure (-0.01MPa).

[0053] ④ It is detected that the residue of the raw material is 0.92%. After the reaction is completed, the isobutanol is distilled off.

[0054] ⑤Add 205g of acetone to the reaction liquid after steaming isobutanol, control the temperature at 38°C, and grow the crystal for 3.5 hours.

[0055] ⑥ After the crystal growth is completed, cool down to 0°C, filter with suction, and wash the material with 70g of acetone.

[0056] ⑦ The product (II) was obtained after vacuum drying at 40°C for 6 hours, with a molar yield of 78.27% and a purity of 98.81%.

[0057] ⑧Steam ...

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Abstract

The invention particularly relates to a synthesis method of a latamoxef intermediate, and belongs to the technical field of synthesis of antibiotic drug intermediates. According to the synthesis method of the latamoxef intermediate, 3,3-dimethyl-6-(4-methyl-benzamido)-4,7-dioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid diphenyl methyl ester is used as a raw material and subjected to a reflux reaction with triethyl phosphite in a solvent isobutanol to obtain the product 3-methyl-2-(7-oxo-3-p-tolyl-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-en-6-yl)-but-3-enoic acid diphenyl methyl ester. The method is simple and easy to implement, the production cost is reduced, the product yield is increased, the solvent is recycled, and the method has high economic value and environmental protection benefits.

Description

technical field [0001] The invention specifically relates to a method for synthesizing an intermediate of latamoxef, and belongs to the technical field of synthesizing intermediates of antibiotic drugs. Background technique [0002] Latamoxef intermediate 3-methyl-2-(7-oxo-3-p-tolyl-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-ene-6- base)-but-3-enoic acid benzhydryl ester is an intermediate of Latamoxef. Latamoxef is a semi-synthetic cephalosporin antibiotic with wide clinical application and increasing market demand. Latamoxef was included in the "National Basic Medical Insurance and Industrial Injury Insurance Drug Catalog" published in September 2004. [0003] Domestic and foreign cephalosporin antibiotic production enterprises need a large amount of 3-methyl-2-(7-oxo-3-p-tolyl-4-oxa-2,6-diazabicyclo[3.2.0]hept-2- En-6-yl)-but-3-enoic acid benzhydryl ester, among them, the Japanese Shionogi Company has a stable market, and its annual demand has been around 20 tons for many yea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/04
CPCC07D498/04
Inventor 周浩张立明周磊常明珠马祥云
Owner YIYUAN XINQUAN CHEM
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