Structural elucidation of an unknown Simvastatin by-product in industrial synthesis starting from Lovastatin.
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.
Bertacche
Vittorio
V
Istituto di Chimica Organica A. Marchesini, Università degli Studi, Milano, Italy.
Milanese
Alberto
A
Nava
Donatella
D
Pini
Elena
E
Stradi
Riccardo
R
D002851:Chromatography, High Pressure Liquid; D008148:Lovastatin / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D019821:Simvastatin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D017550:Spectroscopy, Fourier Transform Infrared; D053719:Tandem Mass Spectrometry
D008148:Lovastatin; D019821:Simvastatin