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Preparation method of moxifloxacin intermediate

A compound and reaction technology, applied in the field of preparation of moxifloxacin intermediates, can solve problems such as low yield, complex process flow, and low chiral selection

Inactive Publication Date: 2020-05-05
XIAMEN GINPOSOME PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The technical problem to be solved in the present invention is to provide a new moxifloxacin intermediate in order to overcome the defects of low chiral selection, complicated process flow and low yield in the preparation method of the existing moxifloxacin intermediate Preparation

Method used

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  • Preparation method of moxifloxacin intermediate
  • Preparation method of moxifloxacin intermediate

Examples

Experimental program
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Effect test

Embodiment 1

[0073]

[0074] The raw material N-Boc-aspartic acid benzylimide can be synthesized according to the literature Tetrahedron Letters 2004,3603.

[0075] Dissolve 304 grams of raw material N-Boc-aspartic acid benzylimide in 2 liters of dimethylformamide, add 40 grams of sodium hydrogen in batches at room temperature, after the addition, stir for one hour, and slowly add dibromide dropwise 404 g of propane, after adding, stir until the TLC detection reaction is complete, add water to quench the reaction, extract with dichloromethane, dry and concentrate to obtain 350 g of an intermediate (compound shown in formula II) with a yield of 82.3% and a content of more than 97%.

[0076] 1 H NMR(400MHz, CDCl 3 )δ:7.40-7.28(5H,m), 4.90-4.83(1H,m), 4.80(2H,s), 3.52(2H,t,J=6.5Hz), 3.09(1H,dd,J=3.5, 8.9Hz), 2.98 (2H, t, J = 6.5 Hz), 2.79 (1H, dd, J = 3.5, 8.9 Hz), 2.10-2.00 (2H, m), 1.45 (9H, s).

[0077] Dissolve 350 g of the intermediate obtained in the previous step in 1400 mL of anhydrous tetr...

Embodiment 2

[0086] Dissolve 304 kilograms of N-Boc-aspartic acid benzylimide in 2000 liters of dimethylformamide, add 40 kilograms of sodium hydrogen in batches, after the addition, stir for one hour, slowly add dibromopropane 404 dropwise After the addition, stir until the reaction is over, add water to quench the reaction, extract with dichloromethane, dry and concentrate to obtain 350 kg of intermediate, with a yield of 82.3%.

[0087] Dissolve 350 kg of the intermediate in 1400 liters of anhydrous tetrahydrofuran, cool to about -70 degrees, dropwise add 420 liters (2M) of a tetrahydrofuran solution of lithium diisopropylamide, and slowly warm up to room temperature after the addition. After the reaction was completed, water was added to quench the reaction, THF was concentrated, and the residue was extracted with water and ethyl acetate, dried and concentrated to obtain 260 kg of the ring-closing product, the yield: 91.8%.

[0088] Heat 260 kg of the ring-closure product with 1000 liters o...

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Abstract

The invention discloses a preparation method of a moxifloxacin intermediate. The invention provides a preparation method of a compound as shown in a formula III, which comprises the following step: ina solvent, in the presence of alkali, carrying out cyclization reaction as shown in the specification on a compound as shown in a formula II to obtain the compound as shown in the formula III. The method is simple to operate, high in chiral selectivity, simple in process, high in yield and high in purity.

Description

Technical field [0001] The invention relates to a preparation method of moxifloxacin intermediate. Background technique [0002] Moxifloxacin is a fourth-generation quinolone antibacterial drug, a new generation antibiotic with a broad antibacterial spectrum. This product has strong antibacterial activity against common respiratory bacteria, such as Streptococcus pneumoniae, Haemophilus influenzae, Moraxella catarrhalis and some Staphylococcus aureus, especially for Streptococcus pneumoniae, with strong antibacterial effect. It is clinically used to treat acute sinus adenitis, acute attacks of chronic bronchitis, community-acquired pneumonia, and uncomplicated skin infections and skin and soft tissue infections. Moxifloxacin is characterized by almost no photosensitivity, good tissue penetration, and high concentration in lung tissue. It is a good medicine for the treatment of respiratory infections. [0003] (S,S)-2,8-diazabicyclo[4,3,0]nonane is an intermediate of moxifloxacin....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C07D207/416
CPCC07B2200/07C07D207/416C07D471/04
Inventor 沈鑫陈颖江王丹詹华杏
Owner XIAMEN GINPOSOME PHARM CO LTD
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