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7-MAC, preparation method therefor and synthesis method for cefminox sodium

A technology for cefminox sodium and methoxy cephalosporin, which is applied in the field of methoxy cephalosporin intermediates and their preparation, and in the field of synthesis of cefminox sodium, can solve the problem of increasing the operational difficulty of post-processing, difficult to guarantee quality control, complicated reaction system, etc. problems, to achieve the effect of taking advantage of energy consumption, avoiding incomplete reaction, and simplifying reaction conditions

Active Publication Date: 2019-03-05
重庆天地药业有限责任公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The above two patented methods are both direct 7-ACA methods, but the process is complicated and requires high anhydrous. At the same time, there are hexamethyldisilazane, acidic reagent thionyl chloride and alkaline reagent in the same reaction system Triethylamine and lithium methoxide, the reaction system is extremely complex, which increases the operational difficulty of post-treatment, and it is difficult to guarantee the quality control, so it is difficult to implement in production

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  • 7-MAC, preparation method therefor and synthesis method for cefminox sodium
  • 7-MAC, preparation method therefor and synthesis method for cefminox sodium
  • 7-MAC, preparation method therefor and synthesis method for cefminox sodium

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preparation example Construction

[0047] Preparation of 7-imidomethan(ethyl)ether cephalosporanic acid

[0048] Protect the 7-amino group of 7-amino 3-[(1-methyltetrazol-5-yl)thiomethyl]cephalosporanic acid with an amino-protecting reagent to prepare 7-imidocephalosporanic acid.

[0049] In a preferred embodiment of the present invention, orthoesters such as triethyl orthoformate, trimethyl orthoformate or trimethyl orthoacetate are used as amino-protecting reagents; in the presence of basic catalysts such as triethylamine, etc., Condensation reaction of 7-amino 3-[(1-methyltetrazol-5-yl)thiomethyl]cephalosporanic acid with orthoester to prepare 7-imide methyl (b) ether cephalosporanic acid ; Preferably, the above reaction can be carried out at 40° C. to 50° C., for example, using dichloromethane as a solvent under reflux conditions.

Embodiment 1

[0051]Add 10g (0.035mol) of 7-TMAC into a three-necked reaction flask, add 80ml of dichloromethane, add 10g of triethylamine, stir for 30min to dissolve, add 7.6g (0.051mol) of triethylorthoformate, heat and reflux for 4 hours, Cool to room temperature, add 100ml of water, stir, separate the water layer, add 20% hydrochloric acid to the water layer to adjust the pH to 1-2, precipitate crystals, filter, and dry in vacuo to obtain white solid 7-imidoethyl ether cephalosporanic acid (7- FACT) 11.13g, yield 95.4%, purity 98.6% (HPLC normalization method).

[0052] NMR H spectrum, Unity INVOA 400 type CDCl3 as solvent, TMS internal standard,

[0053] 1H-NMR(CF3COOD+D2O)δ1.1(d-3H),3.45(m,2H),3.76(m-3H),3.96(m-1H),4.1(q-2H),4.34(m-1H ), 4.83(m-1H), 4.94(m-1H).

[0054] ESI-MS:M / Z 385.1[M+H] + ,407.1[M+Na] + .

Embodiment 2

[0056] Add 10g (0.035mol) of 7-TMAC into a three-necked reaction flask, add 80ml of dichloromethane, add 10g of triethylamine, stir for 30min to dissolve, add 6g (0.056mol) of trimethyl orthoformate, heat to reflux for 4 hours, cool Bring to room temperature, add 100ml of water, stir, separate the water layer, add 20% hydrochloric acid to the water layer to adjust the pH to 1-2, precipitate crystals, filter, and dry in vacuo to obtain 10.49 g of white solid 7-imidomethyl ether cephalosporanic acid, Yield 93.25%, purity 98.3% (HPLC normalization method).

[0057] 1H-NMR(CF3COOD+D2O)δ3.24(s-3H),3.41(m-2H),3.68(m-3H),3.98(m-1H),4.24(m-1H),4.78(m-1H ), 4.95(m-1H).

[0058] ESI-MS:M / Z 373.1[M+H] + ,395.1[M+Na] + .

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Abstract

The invention provides 7-MAC. The 7-MAC has a chemical structure represented by a formula I shown in the description. The invention further provides a preparation method for the 7-MAC and applicationof the 7-MAC and a synthesis method for cefminox sodium. According to the 7-MAC and the synthesis method, provided by the invention, the reaction conditions of preparation of cynnematin (e.g. cefminoxsodium) are simplified, the operability is improved, and meanwhile, the cost is reduced, so that the cynnematin has obvious competitive advantage.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and in particular relates to a metoxyceph intermediate and its preparation method and application. The invention also relates to a synthesis method of cefminox sodium. Background technique [0002] Metoxycephalosporin is a new class of cephalosporins (also known as cephalosporins), including cefoxitin sodium, cefminox sodium, cefbuperazone sodium, cefmetazole sodium, cefotetan and other products, except cephalosporin Except for Siding, the rest of the products currently use the intermediate 7β-amino-7α-methoxy-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]-3-cephem- 4-diphenylmethyl carboxylate (7-MAC) carries out the synthetic route, and the preparation route of 7-MAC and cefminox sodium at present is as follows: [0003] [0004] The specific process is: use 7-aminocephalosporanic acid (7-ACA) as the starting material, protect the carboxyl group with benzhydrin, condense with 1-methyltetrazolium-5-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/18C07D501/57C07D501/04
CPCC07D501/04C07D501/18C07D501/57Y02P20/55
Inventor 吴建军白智全
Owner 重庆天地药业有限责任公司
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