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Intermediate compound for synthesizing Cefradine or Cefroxadine, and preparation method and application thereof

A technology of cephradine and its compound, which is applied in the fields of organic chemistry and bulk chemical production, can solve problems such as complex process, long post-processing operation period, and difficulty in industrial production, achieve high reaction yield, avoid isomerization phenomenon, and be easy to process The effect of industrial production

Inactive Publication Date: 2013-12-18
NANJING FROCHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0025] This method needs to be carried out at a lower temperature, and the post-treatment operation period is long and the process is complicated, which brings certain difficulties to industrial production.

Method used

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  • Intermediate compound for synthesizing Cefradine or Cefroxadine, and preparation method and application thereof
  • Intermediate compound for synthesizing Cefradine or Cefroxadine, and preparation method and application thereof
  • Intermediate compound for synthesizing Cefradine or Cefroxadine, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Preparation of D-2-(tert-butoxycarbonyl)amino-2-(1,4-cyclohexadiene)acetic acid (II)

[0060] Add 15.3g of D-2-amino-2-(1,4-cyclohexadiene) acetic acid, 8g of sodium hydroxide, 150g of water and 150g of THF into the reaction flask, cool to 0°C, add 23.6g of Boc 2 O, keep warm for 2 hours, rise to room temperature, react for 8 hours, recover THF, add ethyl acetate, adjust the pH of the aqueous phase to 3-4 with concentrated hydrochloric acid, separate layers, extract the aqueous phase with ethyl acetate, and combine the organic phases Finally, the organic layer was washed with saturated brine, concentrated and dried to obtain 25 g of crude D-2-(tert-butoxycarbonyl)amino-2-(1,4-cyclohexadiene)acetic acid.

[0061] Similarly, the catalyst can be replaced by potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate or potassium bicarbonate as an option.

Embodiment 2

[0063] Preparation of D-2-(tert-butoxycarbonyl)amino-2-(1,4-cyclohexadiene)acetic acid (II)

[0064] Add 15.3g D-2-amino-2-(1,4-cyclohexadiene) acetic acid, 42g sodium bicarbonate, 306g water, 612g dioxane and 109g Boc 2 O, react at 0°C for 36 hours, recover THF, add DCM, adjust the pH of the aqueous phase to 3-4 with concentrated hydrochloric acid, separate layers, extract the aqueous phase with DCM, combine the organic phases, concentrate and dry to obtain D-2-( 20g of crude product of tert-butoxycarbonyl)amino-2-(1,4-cyclohexadiene)acetic acid.

[0065] Similarly, the catalyst can be replaced by sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate or potassium bicarbonate as an option.

Embodiment 3

[0067] Preparation of D-2-(tert-butoxycarbonyl)amino-2-(1,4-cyclohexadiene)acetic acid (II)

[0068] Add 15.3g of D-2-amino-2-(1,4-cyclohexadiene) acetic acid, 10g of potassium bicarbonate, 76.5g of water and 38.3g of THF into the reaction flask, cool to 0°C, add 21.8g of Boc 2 O, after 2 hours of heat preservation, rise to 35°C, react for 6 hours, recover THF, add ethyl acetate, adjust the pH of the aqueous phase to 3-4 with concentrated hydrochloric acid, separate layers, extract the aqueous phase with ethyl acetate, and combine the organic After phases, the organic layer was washed with saturated brine, concentrated and dried to obtain 22 g of crude product of D-2-(tert-butoxycarbonyl)amino-2-(1,4-cyclohexadiene)acetic acid.

[0069] Similarly, the catalyst can be replaced by sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate or sodium bicarbonate as an option.

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Abstract

The invention relates to an intermediate compound for synthesizing cephradine or cefroxadine, a preparation method and application thereof, and belongs to the field of medicine and chemical industry. The intermediate compound of synthetic cephradine or Cefroxadine of the present invention, its chemical name is: D-2-(tert-butoxycarbonyl) amino-2-(1,4-cyclohexadiene) acetate, its structural formula is as Shown in chemical structural formula I: I wherein, R is or.

Description

technical field [0001] The invention relates to an intermediate compound of cephradine or cefroxadine, a preparation method and application thereof, and belongs to the field of medicine and chemical industry. Background technique [0002] Cefradine (Cefradine) is a semi-synthetic cephalosporin antibiotic successfully researched by Bristol-Myers Squibb in 1972. It belongs to the first generation of cephalosporins. Its structural formula is shown in IV, and its chemical name is (6R,7R)-7-[(R )-2-amino-(1,4-cyclohexadiene)-acetyl]amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4,2,0]-octane -2-ene-2-carboxylic acid monohydrate. Cephradine showed good activity against sensitive bacteria such as Staphylococcus aureus (including penicillin-resistant Gram-positive strains), hemolytic streptococcus, Escherichia coli, Proteus mirabilis, Klebsiella pneumoniae and Haemophilus influenzae. Antibacterial activity, highly resistant to β-lactamase produced by various bacteria; clinically effecti...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/18C07D207/46C07D501/22C07D501/59C07D501/06
CPCY02P20/55
Inventor 马坚陈阳陆静云
Owner NANJING FROCHEM TECH
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