AI Article Synopsis
- - An unknown by-product was discovered in the synthesis of Simvastatin from Lovastatin, specifically during a step where butylamine was replaced with benzylamine in Merck Sharp and Dhome's process.
- - The molecular structure of the by-product was determined using various analytical techniques, including NMR spectroscopy, HPLC/MS, MS/MS, and FT-IR.
- - The isolated compound was identified as alpha,beta,gamma,delta unsaturated Simvastatin N-benzylamide, with the molecular formula C(32)H(43)NO(3) and notable features in its heptanoic acid amide residue.
Article 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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| http://dx.doi.org/10.1016/j.jpba.2007.07.004 | DOI Listing |
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