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Penicillin G sulfoxide composite crystal and preparation method thereof

A composite crystal, penicillin technology, applied in the direction of organic chemistry, can solve problems such as unfavorable use and storage, and achieve the effect of good effect, good use effect and good stability

Active Publication Date: 2010-06-02
NORTH CHINA PHARMA COMPANY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, penicillin G sulfone containing crystal water is not conducive to its use and storage

Method used

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  • Penicillin G sulfoxide composite crystal and preparation method thereof
  • Penicillin G sulfoxide composite crystal and preparation method thereof
  • Penicillin G sulfoxide composite crystal and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] At room temperature, put 10 grams of penicillin G sulfoxide (moisture content 0.2%) into the there-necked flask, add 150 milliliters of methanol, and under stirring at 120 rpm, use a 60°C water bath to heat up the material to 50°C to dissolve to form penicillin G Methanol solution of sulfoxide. The water bath was removed, and the solution was gradually cooled to 10°C with ice water. During this period, methanol complex crystals of penicillin G sulfoxide gradually precipitated, then the ice water was removed, and the material was further cooled to -5°C with ice brine, and filtered. Wash with 10 ml of methanol and dry to obtain 10.5 g (96.6%) of methanol complex crystals of penicillin G sulfoxide.

[0042] Listed below are the X-ray powder diffraction patterns of the obtained crystals obtained by passing copper rays of λ=1.54059 angstroms through a monochromator silk filter.

[0043] X-ray powder diffraction pattern

[0044]

[0045]

[0046] where d is the interp...

Embodiment 2

[0048] At room temperature, put 10 grams of penicillin G sulfoxide with a water content of 20% into the there-necked bottle, add 100 milliliters of methanol and 50 milliliters of water, and stir at 150 rpm, use a 50°C hot water bath externally to heat up the material to 45°C, stirring and dissolving to form penicillin G sulfoxide in methanol aqueous solution. The water bath was removed, and the solution was gradually cooled to 15°C with ice water. During this period, methanol complex crystals of penicillin G sulfoxide gradually precipitated, then the ice water was removed, and the material was further cooled to -10°C with ice brine, and filtered. Wash with 10 ml of methanol and dry to obtain 8.4 g (97%) of methanol complex crystals of penicillin G sulfoxide.

Embodiment 3

[0050]At room temperature, put 10 grams of penicillin G sulfoxide with a water content of 20.0% into the three-necked flask, add 140 ml of methanol, 30 ml of toluene and 28 ml of water, and use a 70°C hot water bath for external use under stirring at 200 rpm , raising the temperature of the material to 60°C, stirring and dissolving to form a mixed solvent solution of penicillin G sulfoxide. The hot water bath was removed, and the temperature of the solution was gradually lowered to 10°C with ice water. During this period, methanol complex crystals of penicillin G sulfoxide were gradually precipitated. The ice water was removed, and the material was further cooled to -5°C with ice brine, and filtered. Wash with 10 ml of methanol and dry to obtain 8.5 g (97.8%) of methanol complex crystals of penicillin G sulfoxide of the present invention.

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Abstract

The invention discloses a novel composite crystal of penicillin G sulfoxide and preparation thereof. The composite crystal has a melting point of 106.9 DEG C., and percentage content of elements are C:53.35%, N:7.23%, O:24.9%, H:5.78%, S:8.70%. The preparation includes steps of: (a) dissolving the penicillin G sulfoxide in a methanol solution, or a solution containing methanol, or a organic solution containing methanol; (b) cooling down the solution containing penicillin G sulfoxide and methanol, turns penicillin G sulfoxide and methanol into saturated state or hypersaturated state gradually,thus crystals are separated. The inventive composite crystal is good in stability, and enhance yield and concentration of cethalosporanic acid effectively in ring-expanding reaction.

Description

technical field [0001] The invention relates to a composite crystal of penicillin G sulfoxide and a preparation method thereof. Background technique [0002] Penicillin G sulfoxide is usually obtained by oxidation of penicillin G as a starting material. It can synthesize various cephalosporanic acids through ring expansion and rearrangement reactions, such as 7-ADCA (7-aminodesacetoxy cephalosporanic acid), GCLE (7-phenylacetamido-3-chloromethyl cephalosporanic acid on methoxybenzyl ester), GCLH (diphenylmethyl 7-phenylacetamido-3-chloromethylcephemate). Penicillin G sulfoxide has a unique molecular structure of β-lactam, which is unstable when exposed to heat, and forms hydrogen bonds with solvents in aqueous solutions, so the product easily forms crystals containing 2 water molecules when it is precipitated in aqueous solution. Since the ring expansion rearrangement reaction is an anhydrous reaction, the technology requires that the water content in the penicillin G sulf...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D499/20
Inventor 平志存王京温同礼米振瑞孙孟生刘云坡闫峰梁雪智张致一杨梦德马金玉郑宝丽高俊艳于辉刘倩刘东甘平娟段志刚袁五锁张锁庆
Owner NORTH CHINA PHARMA COMPANY
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