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Ledipasvir is an antiviral drug that is primarily used to treat chronic hepatitis C infections.
It is a component of a combination therapy that also includes sofosbuvir, and is marketed under the brand name Harvoni.
The chemical structure of ledipasvir is that of a quasi-amide, which is a type of organic compound that contains a carbonyl group (-CO-) attached to a nitrogen atom.
This structure is unique among antiviral drugs, and is believed to contribute to the drug's effectiveness in treating hepatitis C.
The intermediate of ledipasvir is the compound (2S)-2-(2H-benzo[d][1,3]oxazepin-9-yl)-N-(2S,4R)-4-(difluoromethyl)-2-(2-methoxy-1H-imidazo[4,5-f][1,4]benzoxazepin-10-yl)acetamide, which is often referred to by its chemical formula: (2S)-1911883-157-8.
The synthesis of this intermediate involves a number of steps, including the synthesis of the starting materials and their subsequent transformation through a series of chemical reactions.
The process is complex and involves several purification steps to obtain the final product.
The synthesis of ledipasvir's intermediate begins with the synthesis of the starting material (S)-1-(2-(2-hydroxy-1H-benzimidazol-6-yl)-1,3-oxazepin-9-yl)-4-fluoro-2-methyl-1-naphthamide.
This compound is synthesized through a series of chemical reactions that involve the condensation of various reagents, such as lithium hydroxide, 2-fluoro-1-naphthalene, and 6-aminonicotinamide.
After the synthesis of the starting material, it is subjected to a series of chemical reactions that involve the reduction of the nitro group, the introduction of the benzoxazepine ring, and the introduction of the difluoromethyl group.
These reactions are carried out using various chemical reagents and catalysts, such as sodium borohydride, sodium hydroxide, and palladium on barium sulfate.
After the completion of the synthesis of the intermediate, it is purified through a series of chromatographic techniques, such as high-performance liquid chromatography (HPLC) and flash chromatography.
These techniques involve the use of various solvents and adsorbents to separate the intermediate from any impurities that may have been introduced during the synthesis process.
The purified intermediate is then used as the starting material for the synthesis of ledipasvir.
This involves the introduction of the carbonyl group and the amidation step, which are carried out using acetic anhydride and triphenyl phosphine, respectively.
The final step involves the reduction of the nitro group using sodium borohydride, which results in the formation of the final product.
In summary, the intermediate of ledipasvir is synthesized through a series of chemical reactions that involve the synthesis of the starting material and its subsequent transformation through a series of chemical reactions.
The synthesis process is complex and involves several purification steps to obtain the final product.
The intermediate is an important component of the combination therapy that is used to treat chronic hepatitis C infections.