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Penicillin G sulfoxide dimethyl formamide (DMF) composite crystal and preparation method thereof

A technology of composite crystal and penicillin, applied in the field of medicine, can solve the problems of affecting the yield of ring expansion rearrangement reaction, unstable methanol composite crystal, affecting esterification protection reaction, etc., and achieves high stability, simplified solvent system, moisture content and the like. reduced effect

Active Publication Date: 2015-05-20
NORTH CHINA PHARMA COMPANY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the penicillin G sulfoxide methanol complex crystal contains methanol that can damage the esterification agent and the protective agent, which will affect the progress of the esterification protection reaction, thereby affecting the improvement of the yield of the ring expansion rearrangement reaction, and the methanol of penicillin G sulfoxide The affinity between penicillin G sulfoxide and methanol in the complex crystal is not strong, and it is easily replaced by other organic reagents, that is, the methanol complex crystal of penicillin G sulfoxide is unstable

Method used

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  • Penicillin G sulfoxide dimethyl formamide (DMF) composite crystal and preparation method thereof
  • Penicillin G sulfoxide dimethyl formamide (DMF) composite crystal and preparation method thereof
  • Penicillin G sulfoxide dimethyl formamide (DMF) composite crystal and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] At room temperature, put 30 grams of penicillin G sulfoxide (water content 15%) into a 100ml single-mouth eggplant-shaped bottle, add DMF12.8ml, and dissolve in an ultrasonic pool at 35°C to form a DMF mixed solution of penicillin G sulfoxide . Cool the single-mouth eggplant-shaped bottle, make the temperature of the mixed solution drop to -10°C and let it stand for 24 hours, filter to obtain a filter cake, wash the filter cake with 80ml of petroleum ether, and dry to obtain 26.6 grams of penicillin G sulfoxide DMF complex crystals (molar yield 86.3%).

[0043] The X-ray powder diffraction spectrum of the penicillin G sulfoxide DMF composite crystal that embodiment 1 obtains, as shown below, described X-ray powder diffraction spectrum is to pass the monochromator silk filter to obtain by the copper ray of λ=1.54059 angstrom .

[0044]

[0045] where d is the interplanar spacing, and A% is the relative intensity.

[0046] The melting point of the penicillin G sulfo...

Embodiment 2

[0048] At room temperature, put 30 grams of penicillin G sulfoxide (0.3% water content) into a 100ml one-mouth eggplant-shaped bottle, add 30ml of DMF (that is, N,N-dimethylformamide), and carry out in an ultrasonic pool at 30°C Dissolved to obtain a DMF mixed solution of penicillin G sulfoxide. Cool the single-mouth eggplant-shaped bottle, lower the temperature of the mixed solution to -20°C and let it stand for 24 hours, filter to obtain a filter cake, wash the filter cake with 100ml of petroleum ether, and dry to obtain 20.5 grams of penicillin G sulfoxide DMF complex crystals (molar yield 56.6 %), melting point is the heat flow curve measured by differential scanning calorimeter.

[0049] The melting point of the penicillin G sulfoxide complex crystal obtained in Example 2 was measured by differential scanning calorimetry: 101.0°C.

Embodiment 3

[0051] At room temperature, put 25 grams of penicillin G sulfoxide (water content 0.2%) into a 250ml one-mouth eggplant-shaped bottle, add 100ml of the DMF (N,N-dimethylformamide) mother solution in Example 2, and at 40°C, Dissolve in an ultrasonic bath to form a mixed solution of penicillin G sulfoxide in DMF (N,N-dimethylformamide). This one-mouth eggplant-shaped bottle was cooled, the temperature of the mixed solution was lowered to 5° C. and allowed to stand for 24 hours, filtered to obtain a filter cake, which was washed with 80 ml of petroleum ether, and dried to obtain 20.3 grams of penicillin G sulfoxide DMF complex crystals (molar yield 68.5%).

[0052] The melting point of the penicillin G sulfoxide complex crystal obtained in Example 3 was measured by differential scanning calorimetry: 101.6°C.

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Abstract

The invention discloses a penicillin G sulfoxide dimethyl formamide (DMF) composite crystal and a preparation method thereof. The melting point of the composite crystal is not lower than 101 Celsius degrees. The element contents are that 53.6% of carbon (C), 9.9% of nitrogen (N), 22.8% of oxygen (O), 5.9% of hydrogen (H) and 7.55% of sulfur (S). The preparation method is that firstly, the penicillin G sulfoxide is dissolved in the DMF water solution, the water solution containing the DMF or organic solution containing the DMF to obtain the DMF mixed solution of the penicillin G sulfoxide, and then the DMF mixed solution of the penicillin G sulfoxide is cooled and placed quietly, the penicillin G sulfoxide DMF composite crystal is separated out, and the penicillin G sulfoxide DMF composite crystal is filtered, washed and dried. The penicillin G sulfoxide DMF composite crystal is good in stability, low in water content and does not contain impurities to damage protection for the esterification protective reaction. The process of the esterification protective reaction and a ring-enlargement rearrangement reaction is ensured in process of producing cephalosporin alkyl acid. The cephalosporin alkyl acid obtained from the ring-enlargement rearrangement reaction is high in yield and good in quality.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a penicillin G sulfoxide complex crystal and a preparation method thereof. Background technique [0002] Penicillin G sulfoxide (penicillin G sulfoxide), chemical name (2S,5R,6R)-3,3-dimethyl-6-(2-phenylacetamido) 7-oxo-4-thia-1- Azabicyclo[3.2.0]heptane-2-carboxylate sulfoxide, molecular formula C 16 h 18 o 5 N 2 S, molecular weight is 350.2, chemical structure formula is: [0003] . [0004] Penicillin G sulfoxide is usually obtained by oxidation of penicillin G as the starting material. It is a very important intermediate in the conversion of penicillin G to cephalosporins. It can be synthesized by esterification protection, ring expansion rearrangement and other reactions. Various cephalosporanic acids (esters), such as 7-ADCA (7-aminodesacetoxycephalosporanic acid), GCLE (7-phenylacetamido-3-chloromethyl-3-cephalosporanic acid p-methoxybenzyl ester), GCLH (7-phenylacetamido-...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D499/46C07D499/18
Inventor 米振瑞魏青杰段志钢付成名张苗静郑宝丽闫峰王立强米建伟张伟
Owner NORTH CHINA PHARMA COMPANY
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