Improved Synthesis of Cefdinir and Its Polymorphic Form, an Antibacterial Active Pharmaceutical Ingredient

New methods for the preparation of Cefdinir 1 and its polymorphic form Sesqui hydrate 1a are described. The synthesis of 2-mercaptobenzothiazolyl (Z)-2-(2-amino-4-thiazolyl)-2-acetoxyiminoacetate 4 was affected by using triphenylphosphine and triethylamine, and acylation of 7-amino-3-vinylcephem-4-c...

Full description

Saved in:
Bibliographic Details
Published in:Synthetic communications 2007-07, Vol.37 (13), p.2275-2283
Main Authors: Prasada Rao, Korrapati V. V., Dandala, Ramesh, Sivakumaran, Meenakshisunderam S., Rani, Ananta, Naidu, Andra
Format: Article
Language:English
Subjects:
antibacterial drug
Cefdinir
impurities
synthesis
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:New methods for the preparation of Cefdinir 1 and its polymorphic form Sesqui hydrate 1a are described. The synthesis of 2-mercaptobenzothiazolyl (Z)-2-(2-amino-4-thiazolyl)-2-acetoxyiminoacetate 4 was affected by using triphenylphosphine and triethylamine, and acylation of 7-amino-3-vinylcephem-4-carboxylic acid 5 followed by deprotection with K 2 CO 3 in the presence of ammonium chloride in the same pot yielded crude Cefdinir. Purification of crude Cefdinir through resin and treatment of the resulting wet product with trifluoroacetic acid gave highly pure TFA salt of Cefdinir 6, which on neutralization afforded 1a in excellent yield. The impurity profiling of this compound has also been discussed.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397910701397284