Unknown by-product in Simvastatin synthesis from Lovastatin was found. The elucidation of this molecular structure by means of 1H and 13C 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 32H 43NO 3. The proposed structure of this compound, characterised by the presence of a conjugated dienic system in the heptanoic acid amide residue, was α,β,γ,δ unsaturated Simvastatin N-benzylamide.
Structural elucidation of an unknown Simvastatin by-product in industrial synthesis starting from Lovastatin / V. Bertacche, A. Milanese, D. Nava, E. Pini, R. Stradi. - In: JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS. - ISSN 0731-7085. - 45:4(2007), pp. 642-647.
Structural elucidation of an unknown Simvastatin by-product in industrial synthesis starting from Lovastatin
V. Bertacche;D. Nava;E. Pini;R. Stradi
2007
Abstract
Unknown by-product in Simvastatin synthesis from Lovastatin was found. The elucidation of this molecular structure by means of 1H and 13C 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 32H 43NO 3. The proposed structure of this compound, characterised by the presence of a conjugated dienic system in the heptanoic acid amide residue, was α,β,γ,δ unsaturated Simvastatin N-benzylamide.
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