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US 2014/0148595 A1Published application
Method for the preparation of carbapenam compounds
AssigneeInstytut Chemi Organicznej Pan
InventorsMarek Chmielewski, Bartlomiej Furman, Sebastian Stecko, Irma Panfil, Margarita Jurezak, Paulina Mikolajezyk, Magdalena Soluch
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Abstract
The subject of the present invention is a method of the preparation of compounds containing the core skeleton of carbapenem antibiotics, novel intermediate compounds used in this method, a method of the preparation of the intermediate compounds as well as the use of the intermediate compounds in the production of carbapenem antibiotics.
Claims19
A method of preparing a β-lactam compound defined by the formula 9,
- where:
- R1 denotes a linear or branched substituent:
- a C1-6 alkyl, C3-6-alkene, C1-6-alkoxymethyl, benzyloxymethyl, a hydroxy-C1-6-alkyl, an O-protected hydroxy-C1-6-alkyl, a dihydroxy-C1-6-alkyl or an O,O′-protected dihydroxy-C1-6-alkyl wherein both hydroxyl groups may have the same or different protecting groups, and further wherein the protection of both hydroxyl groups is by a cyclic acetal or ketal group,
- R2 denotes a linear or branched C-alkyl, allyl, benzyl, substituted benzyl, silyl, C1-6-alkoxymethyl, benzyloxymethyl, C1-6-alkylsulphonyl, arylsulphonyl or acyl group;
- R3 denotes an C1-6-alkyl, allyl, benzyl, substituted benzyl, silyl, C1-6-alkoxymethyl, benzyloxymethyl, C1-6-alkylsulphonyl, arylsulphonyl or acyl group;
- R2 and R3 may denote a cyclic acetal or ketal group;
- R4 denotes a hydrogen atom, or methyl, C1-6-alkoxyl, C1-6-alkoxymethyl, allyl benzyloxymethyl, benzyloxyl, siloxyl or acyloxyl group;
- characterised in that a reaction is carried out based on a reaction of an acetylene compound 10
- R1≡ 10
- where R1 has the above meaning, with nitrone defined by the general formula 11
- where R2, R3, R4 have the above defined meaning, in the presence of copper salt, a base and optionally a solvent.
8 more elements
A β-lactam compound of formula 9
- produced by a process comprising the steps of:
- reacting the acetylene compound of formula 10
- R1≡ 10
- with a nitrone compound of formula 11
- in the presence of copper salt;
- wherein R1 is a compound selected from the group consisting of:
- a C1-6 alkyl, C3-6-alkene, C1-6-alkoxymethyl, benzyloxymethyl, a hydroxy-C1-6-alkyl, an O-protected hydroxy-C1-6-alkyl, a dihydroxy-C1-6-alkyl or an O,O′-protected dihydroxy-C1-6 alkyl;
- R2 denotes a linear or branched C-alkyl, allyl, benzyl, substituted benzyl, silyl, C1-6-alkoxymethyl, benzyloxymethyl, C1-6-alkylsulphonyl, arylsulphonyl and acyl group;
- R3 is a substituent selected from the group consisting of an C1-6-alkyl, allyl, benzyl, substituted benzyl, silyl, C1-6-alkoxymethyl, benzyloxymethyl, C1-6-alkylsulphonyl, arylsulphonyl and acyl group;
- R2 and R3 may form a cyclic acetal or ketal group;
- and
- R4 is a compound selected from the group consisting of a hydrogen atom, or methyl, C1-6-alkoxyl, C1-6-alkoxymethyl, allyl benzyloxymethyl, benzyloxyl, siloxyl or acyloxyl group.
9 more elements
Dependencies are inferred from the claim text.