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Method for preparing cefcapene pivoxil hydrochloride

A technology of cefcapene hydrochloride and iodomethyl pivalate, which is applied in the field of medicine and chemical industry, can solve the problems of low purity and low yield of cefcapene hydrochloride, and achieve the advantages of purity, short route and simple synthesis operation Effect

Inactive Publication Date: 2016-11-09
陕西思尔生物科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The invention provides a preparation method of cefcapene pivoxil hydrochloride, which solves the problems of low purity and low yield of cefcapene pixil hydrochloride prepared in the prior art, and provides guarantee for the quality and cost of subsequent products

Method used

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  • Method for preparing cefcapene pivoxil hydrochloride
  • Method for preparing cefcapene pivoxil hydrochloride
  • Method for preparing cefcapene pivoxil hydrochloride

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Embodiment 1: the synthesis of cefcapene pivoxil hydrochloride

[0024] Add 200g of dichloroethane into the three-necked flask, add 20g of BCN under stirring, stir at room temperature 25°C, then start to cool down to -25°C~-20°C, start to add 25.7g of iodine ester dropwise at T=-20°C, keep at -25 ℃~-20℃ and stirred for 3h.

[0025] Post-treatment: Add 200g EA and 300g water to the system, stir and extract at room temperature 25°C; separate layers, and extract the water layer with 100EA again. Combine the EA layers, wash the EA layer once with 300g of saturated sodium bicarbonate, wash the EA layer once with 350g of saturated saline, dry and decolorize the EA layer, concentrate to a solid, add 2 times of EA after weighing, dissolve it, and drop it into 400g of petroleum ether Stir and precipitate, and filter to obtain light yellow solid powder.

[0026] Obtain (Ⅱ) compound, yield: 85%~90%, LC: 99%;

[0027] Under the protection of nitrogen, add 200ml of hydrogen chlor...

Embodiment 2

[0029] Embodiment 2 The identification of product in the embodiment of the present invention 1

[0030] Identification method: Bruker Avance III 400MHz superconducting NMR spectrometer

[0031] Analysis method: LC (liquid chromatography purity), Shimadzu LC-10AT VP, Shimadzu C-18 chromatographic column,

[0032] Mobile phase: acetonitrile: water = 65:35, flow rate 2ml / min.

[0033] 1H NMR ( 500 MHz, ( CD3 ) 2 SO) δ : 0. 97 ~ 1. 01 ( m, 3H), 1. 15 ( s, 9H), 2. 12 ~ 2. 21 ( m, 2H), 3 .50( d, J = 18. 5 Hz, 1H), 3. 60 ( d, J = 18. 5Hz, 1H), 4. 55 ( d, J = 13. 0Hz, 1H), 4. 79 ( d , J = 13. 0 Hz, 1H ), 17( d, J = 5.0 Hz, 1H), 5. 79 ~ 5. 82( m, 2H), 5. 87( d, J = 5. 0 Hz, 1H ), 6. 23( t, J = 7. 5Hz, 1H), 6. 51 ~ 73( m, 2H), 7. 14( s, 1H), 9. 27( d, J = 8. 0Hz, 1H ).

[0034] 7-[2-(2-amino-1,3-thiazol-4-yl)pent-3-enamido]-3-(carbamoyloxymethyl)-8-oxo-5 provided by the present invention -Compared with other synthetic methods, the synthetic method of -thio-1-azabicyclo[4.2.0]oct-2...

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Abstract

The invention discloses a method for preparing an important third-generation oral cephalosporin antibiotic, namely cefcapene pivoxil hydrochloride. BCN is dissolved in dichloroethane and is in docking with 4-side-chain iodomethyl pivalate, then 7-amino BOC protection is removed by means of an ethyl acetate solution of hydrogen chloride, amino hydrochloride is generated directly, finally amino hydrochloride and a diluted hydrochloric acid aqueous solution are recrystallized in methyl alcohol, and white crystal of Cefcapene pivoxil hydrochloride with one molecular of water is obtained. According to the method, the number of synthesis steps is small, cost is low, materials in use are cheap and easy to obtain, industrial production is benefited, and pollution is little.

Description

technical field [0001] The invention belongs to the technical field of medicine and chemical industry, in particular to a preparation method of cefcapene hydrochloride. Background technique [0002] Cefcapene pivoxil is a third-generation oral cephalosporin antibiotic. It is a new type of cephalosporin antibiotic developed by Shionogi Company in Japan. It has strong antibacterial activity against Gram-positive and negative bacteria. [0003] Cefcapene pivoxil hydrochloride, chemical name: (6R,7R)-3-(((carbamoyl)oxy)methyl)-7-(((2Z)-2-(2-amino-4-thiazolyl )-1-oxo-2-pentene)amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (2,2-di Methyl-1-oxopropoxy) methyl ester hydrochloride monohydrate, there are many reports about its synthetic method at present, but there are various problems. [0004] Ishikura K et al. (The Journal of Antibiotics.1994, 466-476) disclose a synthetic method of cefcapene pivoxil, which uses 7-aminocephalosporanic acid as a raw material a...

Claims

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Application Information

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IPC IPC(8): C07D501/34C07D501/04
CPCC07D501/34C07D501/04
Inventor 王作弟
Owner 陕西思尔生物科技有限公司
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