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EP0119431A1 Expired / Lapsed EP ⏱️ 0.0 years remaining

Method of preparing erythromycin A cyclic 11,12-carbonate

Assignee: Tarchominskie Zaklady Farmaceutyczne "Polfa"
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Filing: 1984-02-07
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Granted: —
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Expires: 2004-02-07
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Abstract

Abstract The invention solves the problem of the industrial method of production of erythromycin A cyclic 11,12-carbonate by transesterification of 1,2-diole or 1,3-diole carbonates by means of anhydrous erythromycin A or its salts in anhydrous organic solvents or in the medium of a transesterified substrate in the presence of a phase transfer catalyst (PTC). According to the invention quarternary ammonium and phosphonium compounds may be used in the transesterification process with addition of inorganic compounds, such as salts, alkali metal or alkaline earth metal oxides or hydroxides. Ammonium or phosphonium hydroxides or carbonates do not require any addition of inorganic compounds. According to the invention, as catalysts of the PTC type there may also be used coronary ethers and cryptands with addition of inorganic compounds. As quarternary ammonium compounds there are used salts, such as triethylbenzylammonium (TEBA) chloride or carbonate, tetrabutylammonium bromide, trioctylmethylammonium chloride, whereas among phosphonium compounds there are advantageously used tetrabutylphosphonium chloride or carbonate. Among crown ethers there is used 1,4,7,10,13,16-hexaoxacyclo-octadecane and among cryptands 4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8,8,8]-hexacosane.

Inventors

  • 👤 Marek Dr. Ing. Biedrzycki
  • 👤 Halina Prof. Dr. Ing. Dahlig
  • 👤 Piotr Chmielnicki
  • 👤 Tadeusz Dr. Ing. Glabski

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-09 07:35
CPC Classifications
C; C07; C07H; C07H17/00; C07H17/04; C07H17/08

Claims Analysis

Total Claims: 8
Claim 1
Independent Claim 142 words
Method of preparing erythromycin A cyclic 11,12-carbonate by transesterification of ethylene carbonate, using dehydrated erythromycin or its salts, characterized in that the transesterification process of cyclic 1,2-diole and 1,3-diole carbonates in an anhydrous organic solvent, advantageously either in toluene, in acetone or in an anhydrous cyclic diole carbonate, is performed in the presence of either a quarternary ammonium or phosphonium compound or of one of these compounds as a PTC catalyst with addition of either an inorganic salt, an alkali metal or alkaline earth metal hydroxide or oxide or their mixture or else the process of esterification is performed in the presence of a catalyst of the PTC type, such as a crown ether or a cryptand with the addition of the . above mentioned inorganic compounds or of their mixture, the obtained erythromycin A cyclic 11,12-carbonate being subsequently separated and purified.
Claim 2
Dependent Claim 142 words
Method of preparing erythromycin A cyclic 11,12-carbonate by transesterification of ethylene carbonate, using dehydrated erythromycin or its salts, characterized in that the transesterification process of cyclic 1,2-diole and 1,3-diole carbonates in an anhydrous organic solvent, advantageously either in toluene, in acetone or in an anhydrous cyclic diole carbonate, is performed in the presence of either a quarternary ammonium or phosphonium compound or of one of these compounds as a PTC catalyst with addition of either an inorganic salt, an alkali metal or alkaline earth metal hydroxide or oxide or their mixture or else the process of esterification is performed in the presence of a catalyst of the PTC type, such as a crown ether or a cryptand with the addition of the . above mentioned inorganic compounds or of their mixture, the obtained erythromycin A cyclic 11,12-carbonate being subsequently separated and purified.
Claim 3
Dependent Claim 26 words
Method according to claim 1, characterized in that in the process of transesterifioation there are used cyclic 1,2-diole carbonates, advantageously ethylene carbonate or propylene carb-, onate.
Claim 4
Dependent Claim 21 words
Method according to claim 1, characterized in that in the process'of transesterification there are used cyclic 1,3-diole carbonates, advantageously trimethylene carbonate.
Claim 5
Dependent Claim 53 words
Method according to claim 1, characterized in that as a quarternary ammonium compound there are advantageously used either triethylbenzylammonium chloride, tetrabutylammonium bromide, trioctylmethylammonium chloride with addition of either an inorganic salt, of an alkali metal or an alkaline earth metal hydroxide or oxide or of their mixture or triethylbenzylammonium hydroxide or carbonate alone.
Claim 6
Dependent Claim 48 words
Method according to claim 1, characterized in that as a phosphonium compound there is advantageously used either tetrabutylphosphonium chloride with addition of either an inorganic salt, of an alkali metal or alkaline earth metal hydroxide or oxide or of their mixture or tetre- butylphosphonium hydroxide or carbonate alone.
Claim 7
Dependent Claim 28 words
Method according to claim 1, characterized in that as a -crown ether there is advantageously used ether containing 12 carbon atoms and . 6 oxygen atoms, named 1,4,7,10,13,16-hexaoxacyclo-octadecane.
Claim 8
Dependent Claim 17 words
Method according to claim 1, characterized in that as a cryptand there is advantageously used 4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo- [8,8,8]hexacosane.

References Cited (Backward Citations)

US3417077A Cited

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