Claims
- 1. Process for the preparation of 9-deoxo-8a-aza-8a-homoerythromycin A of formula V
- 2. Process according to claim 1, characterized in that the Beckmann rearrangement is carried out using sulfonyl chloride, preferably selected from tosyl chloride, benzenesulfonyl chloride and mesyl chloride.
- 3. Process according to claim 1, characterized in that the hydrocarbon is selected from linear-, branched- or cyclic-chain hydrocarbons comprising 5 to 15 carbon atoms, in particular from pentane, cyclohexane, methylcyclohexane and heptane, and is preferably heptane.
- 4. Process according to claim 1, characterized in that the organic solvents present in the mixture for the Beckmann rearrangement, comprising pyridine, are removed by separation by settling.
- 5. Process according to claim 1, characterized in that, after removing the organic solvents, including pyridine, from the Beckmann rearrangement mixture, the solvent for the reduction reaction, which is water, is added to the residue.
- 6. Process according to claim 1, characterized in that, after removing the organic solvents, including pyridine, from the Beckmann rearrangement mixture, the solvent for the reduction reaction, which is an organic solvent selected from C1-C10 alcohols, preferably methanol or isopropanol, or which is a mixture of a preceding solvent and water, is added to the residue.
- 7. Process according to claim 1, characterized in that, after removing the organic solvents, including pyridine, from the Beckmann rearrangement mixture, the solvent for the reduction reaction, which is of amide type and which is preferably N,N-dimethylformamide or N,N-dimethylacetamide, or which is a mixture of a preceding solvent and water, is added to the residue.
- 8. Process according to claim 1, characterized in that, after removing the organic solvents, including pyridine, from the Beckmann rearrangement mixture, the solvent for the reduction reaction, which is of cyclic urea type, preferably 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone (DMPU) or 1,3-dimethyl-2-imidazolinone (DMEU), or which is a mixture of a preceding solvent and water, is added to the residue.
- 9. Process according to claim 1, characterized in that the reduction reaction is carried out with sodium borohydride or potassium borohydride.
- 10. Process according to claim 1, characterized in that the compound of formula V formed on conclusion of the reduction reaction is not isolated from the reaction mixture and is directly converted therein by addition of a sufficient amount of an aldehyde R′CHO to result in a compound of formula VII
- 11. Process according to claim 10, characterized in that the aldehyde used is a C1 to C4 aldehyde.
- 12. Process according to claim 10, characterized in that formaldehyde is used as aldehyde to result in 9-deoxo-8a-aza-8a-methyl-8a-homoerythromycin A of following formula VI:
Priority Claims (1)
Number |
Date |
Country |
Kind |
00 03807 |
Mar 2000 |
FR |
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RELATED APPLICATIONS
[0001] This application claims priority from U.S. application Ser. No. 60/198,721, filed Apr. 20, 2000, and from French application 00 03807, filed Mar. 24, 2000. Each of the foregoing applications, and all documents cited therein or during their prosecution (“appln cited documents”) and all documents cited or referenced in the appln cited documents, and all documents cited or referenced herein (“herein cited documents”) and all documents cited or referenced in herein cited documents, together with any manufacturer's instructions, descriptions, product specifications, and product sheets for any products mentioned herein, are hereby incorporated herein by reference.
Provisional Applications (1)
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Number |
Date |
Country |
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60198721 |
Apr 2000 |
US |