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A kind of preparation method of cefcapine hydrochloride

A technology for cefcapine hydrochloride and cefcapine axetil, which is applied in the field of preparation of removing Boc protective groups in the production process of cefcapine hydrochloride, can solve the problems of cumbersome operation, low yield and little difference, etc.

Active Publication Date: 2021-08-20
深圳博泰尔生物技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Most of the existing processes use N-Boc-protected cefcapene proxetil as an intermediate, use trifluoroacetic acid to remove the protecting group, and then form a salt, which has difficulties in handling and unstable materials, and is not suitable for industrial scale-up production
CN102796117 discloses that the cefcapene pivoxil hydrochloride monohydrate is obtained by removing the Boc protection of N-Boc-protected cefcapene pivoxil through acid, and then salting to obtain cefcapene pixil hydrochloride monohydrate. Although this method is a one-pot method, it is slightly improved compared with the conventional method, but There is little difference in essence, the operation is cumbersome, and the yield is not high

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Add acetonitrile (375mL), 4N hydrochloric acid (56.3mL), 3.2g trifluoroacetic acid to the reaction vessel, cool down to -10-0°C while stirring, add N-Boc-protected cefcapene pivoxil (75g), and stir for 120min , recrystallized, centrifuged, the crude product was washed with water (500mL*3), and dried to obtain the fine product of cefcapene hydrochloride monohydrate (65g).

Embodiment 2

[0023] Add acetonitrile (375mL), 4N hydrochloric acid (56.3mL), 2.56g trifluoroacetic acid to the reaction vessel, cool down to -10-0°C while stirring, add N-Boc-protected cefcapene pivoxil (75g), and stir for 120min , recrystallized, centrifuged, the crude product was washed with water (500mL*3), and dried for 20 hours to obtain the fine product of cefcapene hydrochloride monohydrate (58g).

Embodiment 3

[0025] Add acetonitrile (375mL), 4N hydrochloric acid (56.3mL), and 5.13g of trifluoroacetic acid to the reaction vessel, keep stirring at -10-0°C, add N-Boc-protected cefcapene pivoxil (75g), and stir for 120min. Recrystallize, centrifuge, wash the crude product with water (500mL*3), wash the crude product with water (500mL*3), and dry for 20 hours to obtain cefcapine hydrochloride monohydrate fine product (60g).

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PUM

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Abstract

The invention discloses a one-step preparation method of antibiotic drug cefcapene pivoxil hydrochloride monohydrate, comprising the following steps: adding hydrochloric acid and trifluoroacetic acid into an organic solvent, stirring and cooling down to 0 to -10°C, adding Boc The base-protected cefcapene pivoxil is continued to keep warm and stirred, and the reaction is completed, crystallized and filtered, and dried to obtain cefcapene pivoxil hydrochloride monohydrate; the molar ratio of hydrochloric acid and trifluoroacetic acid is 10:1 to 5:1. The preparation method of cefcapene axetil hydrochloride provided by the invention has high yield, low cost, convenient treatment, good stability, mild reaction conditions, environmental protection, and is suitable for industrialized production.

Description

technical field [0001] The invention relates to a preparation method of cefcapene pivoxil hydrochloride, in particular to a preparation method for removing the Boc protecting group in the production process of cefcapene pixil hydrochloride. Background technique [0002] The chemical name of cefcapene pivoxil hydrochloride is 7-[2-(2-amino-1,3-thiazol-4-yl)pent-3-enamido]-3-(carbamoyloxymethyl)-8 -Oxo-5-thio-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethylpropionyloxymethyl ester hydrochloride monohydrate. [0003] Cefcapene pivoxil hydrochloride is the third generation of oral cephalosporin antibiotics. Pharmacological studies have shown that the MIC80 against MSSA of aerobic G+ bacteria is 3.13 μg / ml, which is the same as that of cefotiam and cefaclor, and the MIC80 against Streptococcus pneumoniae ≤0.1μg / ml, superior to cefaclor, comparable to cefditoren, highly active against penicillin-resistant (including moderately resistant) Streptococcus pneumoniae, with ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D501/04C07D501/34
CPCC07D501/04C07D501/34Y02P20/55
Inventor 毛桃
Owner 深圳博泰尔生物技术有限公司
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