Literature DB >> 17697761

Structural elucidation of an unknown Simvastatin by-product in industrial synthesis starting from Lovastatin.

Vittorio Bertacche1, Alberto Milanese, Donatella Nava, Elena Pini, Riccardo Stradi.   

Abstract

Unknown by-product in Simvastatin synthesis from Lovastatin was found. The elucidation of this molecular structure by means of (1)H and (13)C NMR spectroscopy, HPLC/MS, MS/MS and FT-IR was shown. The mentioned by-product, originated during Merck Sharp and Dhome synthesis scheme was isolated in the second-last step replacing butylamine with benzylamine. The spectroscopic results agreed with a molecular formula C(32)H(43)NO(3). The proposed structure of this compound, characterised by the presence of a conjugated dienic system in the heptanoic acid amide residue, was alpha,beta,gamma,delta unsaturated Simvastatin N-benzylamide.

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Year:  2007        PMID: 17697761     DOI: 10.1016/j.jpba.2007.07.004

Source DB:  PubMed          Journal:  J Pharm Biomed Anal        ISSN: 0731-7085            Impact factor:   3.935


  2 in total

1.  Effects of highly hygroscopic excipients on the hydrolysis of simvastatin in tablet at high relative humidity.

Authors:  W L Chen; D W Guo; Y Y Shen; S R Guo; K P Ruan
Journal:  Indian J Pharm Sci       Date:  2012-11       Impact factor: 0.975

2.  Synthesis, characterization and quantification of simvastatin metabolites and impurities.

Authors:  Manish S Bhatia; Swapnil D Jadhav; Neela M Bhatia; Prafulla B Choudhari; Kundan B Ingale
Journal:  Sci Pharm       Date:  2011-07-25
  2 in total

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