This paper describes the facile synthesis of sildenafil citrate (1) and its related compounds through an improved chlorosulfonation reaction using chlorosulfonic acid and thionyl chloride. This synthesis results in pure sildenafil with high yield. The structures of the compounds were determined with infrared (IR), 1H-NMR and 13C-NMR spectroscopic methods, and high resolution mass spectroscopy (HRMS) analysis.
A new degradant of Nafcillin Sodium was found at a level of 1.8% w/w during the gradient reversed-phase HPLC analysis in stability storage samples. This impurity was identified by LC-MS and was characterized by 1H-NMR, 13C-NMR, LC/MS/MS, elemental analysis, and IR techniques. Based on the structural elucidation data, this impurity was named as N-[(2S)-2-carboxy-2-{[(2-ethoxynaphthalen-1-yl)carbonyl]amino}ethylidene]-3-({N-[(2-ethoxynaphthalen-1-yl)carbonyl]glycyl}sulfanyl)-D-valine. This impurity was prepared by isolation and was co-injected into the HPLC system to confirm the retention time. To the best of our knowledge, this impurity has not been reported elsewhere. The identification and structural elucidation of this degradant impurity has been discussed in detail.
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