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Method of preparing cefprozil parent nucleus 7-amino-3-propenylcephalosporanic acid

A technology of propenyl cephalosporanic acid and cefprozil mother nucleus, which is applied in the direction of organic chemistry, can solve the problems of unstable quality, high cost, and low yield, and achieve the effect of low price, low cost, and high yield

Inactive Publication Date: 2010-05-26
SHANGHAI JUNJIE BIOCHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Solve the problems of low yield, high cost and unstable quality in the process of synthesizing 7-APCA with GCLE, which is relatively expensive and in short supply.

Method used

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  • Method of preparing cefprozil parent nucleus 7-amino-3-propenylcephalosporanic acid
  • Method of preparing cefprozil parent nucleus 7-amino-3-propenylcephalosporanic acid
  • Method of preparing cefprozil parent nucleus 7-amino-3-propenylcephalosporanic acid

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Step 1: At room temperature, add 12g of 7-ACA, 100ml of dichloromethane, 10g of hexamethyldisilazane (HMDS), 1ml of trimethylchlorosilane into a dry reaction flask, and raise the temperature to 40-55°C under nitrogen protection , reflux for 7-8 hours, and when it is detected that there is almost no ammonia escape in the reflux tail gas, the reflux is stopped and the temperature is lowered to 0-5° C. to obtain a silylated solution of 7-ACA. 13.5 g of triphenylphosphine was added to the reaction liquid, and 11.5 g of iodotrimethylsilane was added in about 10 minutes, and the temperature should not be higher than 5°C. After the addition is complete, keep the reaction at 5-10°C for 3-5 hours, take a sample to detect that the 7-ACA residue is less than 0.5g / L (HPLC), after the reaction is completed, cool down to -5-0°C to obtain a mixture of compound (3) .

[0030] Step 2 Add 87ml of DMF to the mixed solution of compound (3) obtained in step 1, control the temperature at 0-...

Embodiment 2

[0033] Step 1. At room temperature, add 12g of 7-ACA and 100ml of dichloromethane to the dry reaction flask, cool down to 0-5°C, add 13.5g of triphenylphosphine, and add 33g of iodotrimethylsilane within about 10 minutes. The temperature shall not be higher than 5°C. After the addition is complete, keep the reaction at 5-10°C for 3-5 hours, take a sample to detect that the 7-ACA residue is less than 0.5g / L (HPLC), after the reaction is completed, cool down to -5-0°C to obtain a mixture of compound (3) .

[0034] Subsequent operation is the same as embodiment one, and the result is the same.

Embodiment 3

[0036] Step 1, step 2 are the same as embodiment 1.

[0037] Step 3: Vacuum distill the mixture of compound (4) obtained in step 2 to remove dichloromethane. The distillation temperature is controlled below 50°C. After the distillation is complete, cool down to room temperature, add 5g of activated carbon, stir for 30 minutes, and filter. Add 400ml of water to the filtrate, heat up to 35-40°C, keep stirring for 30 minutes, cool down to 0-5°C, stir for 1 hour, filter, and wash with 50ml of water and 100ml of acetone. Vacuum drying at 35°C for 7-8 hours gave 10.2 g of 7-APCA with a purity of 95.5% (HPLC cis / trans = 92.5 / 7.5). Yield 78%.

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Abstract

The invention discloses a new making method of cepham propone parent nucleus 7-amino-3-propenyl cepham alkyl acid (7-APCA), which comprises the following steps: reacting 7-ACA(2) protected by silicaneand substituted by iodine with triphenylphosphor in the solvent during -10-120 deg. c; obtaining the compound (3); reserving the compound (3) in the alkaline metal salt; reacting the compound (3) andacetaldehyde to obtain the compound (4); crystallizing the compound (4) through removing the protector; obtaining the product to synthesize the cepham propone.

Description

technical field [0001] The invention relates to a new method for preparing cefprozil core nucleus 7-amino-3-propenyl cephalosporanic acid (7-APCA), the structure of which is shown in (1). The cefprozil mother nucleus is a raw material for preparing cefprozil. [0002] [0003] 7-APCA(1) Background technique [0004] The chemical name of Cefprozil is (6R,7R)-7-(R)-2-amino-2-(p-hydroxyphenyl)acetamido-8-oxo-3-(1-propenyl)-5 -Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid monohydrate is a second-generation oral cephalosporin with broad-spectrum antibacterial activity. [0005] At present, the reported methods for synthesizing 7-APCA basically adopt the GCLE route, such as US Patent No. US4694079, US2004132992, Chinese Patent Publication No. CN1694888 and so on. The synthetic route is as follows: [0006] [0007] Using GCLE as raw material to synthesize 7-APCA, the synthesis yield is low, and the mol yield is about 60%, and there are disadvantages such as long sy...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D501/18
Inventor 陈舒明方长明
Owner SHANGHAI JUNJIE BIOCHEM TECH
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