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US 9,040,688 B2Granted
Intermediates in the preparation of 1,4-diphenyl azetidinone
AssigneeLupin Limited
InventorsDhananjai Srivastava, Rajiv Kumar Shakya, Namrata Anil Chaudhari, Inamus Saqlain Ansari, Girij Pal Singh
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Abstract
The process of the present invention relates to a method for the synthesis of a 1,4-diphenylazetidinone of formula (VIII) by using novel oxime intermediates.
Claims9
A process for the preparation of the compound of formula (VIII),
- the process comprising the steps of
- a) reacting hydroxylamine or its derivative with a ketone of formula (I) to obtain an oxime of formula (II) wherein R=H, alkyl or silyl;
- b) reacting the oxime of formula (II) with an imine of formula (III), wherein R′=H or any phenolic protecting group to obtain β-(substituted-amino)amide of formula (IV);
- c) cyclizing the β-(substituted-amino)amide of formula (IV) to form an azetidinone of formula (V);
- d) converting the oxime functionality in the compound of formula (V) to a ketone of formula (VI);
- e) reducing the ketone functionality of a compound of formula (VI) to the alcohol of formula (VII);
- f) removing the phenolic protecting group at any desired stage in the above synthesis.
4 more elements
A process for the preparation of the compound of formula (VIII),
- the process comprising the steps of
- a) reacting the oxime of formula (II), wherein R=H, alkyl or silyl;
- with an imine of formula (III), wherein R′=H or any phenolic protecting group to obtain β-(substituted-amino)amide of formula (IV);
- b) cyclizing the β-(substituted-amino)amide of formula (IV) to form an azetidinone of formula (V);
- c) converting the oxime functionality in the compound of formula (V) to a ketone of formula (VI);
- d) reducing the ketone functionality of a compound of formula (VI) to the alcohol of formula (VII);
- e) removing the phenolic protecting group at any desired stage in the above synthesis.
4 more elements
A process for the preparation of the compound of formula (VIII),
- the process comprising the steps of
- a) cyclizing the β-(substituted-amino)amide of formula (IV), wherein R=H, alkyl or silyl and R′=H or any phenolic protecting group, to form an azetidinone of formula (V);
- b) converting the oxime functionality in the compound of formula (V) to a ketone of formula (VI);
- c) reducing the ketone functionality of a compound of formula (VI) to the alcohol of formula (VII);
- d) removing the phenolic protecting group at any desired stage in the above synthesis.
2 more elements
A process for the preparation of the compound of formula (VIII),
- the process comprising the steps of
- a) converting the oxime of formula (V), wherein R=H, alkyl or silyl and R′=H or any phenolic protecting group, to a ketone of formula (VI);
- b) reducing the ketone functionality of a compound of formula (VI) to the alcohol of formula (VII);
- removing the phenolic protecting group at any desired stage in the above synthesis.
1 more element
Dependencies are inferred from the claim text.