Ledipasvir

Base Information

• Chemical Name: Ledipasvir
• CAS No.: 1256388-51-8
• Molecular Formula: C49H54F2N8O6
• Molecular Weight: 889.015
• Hs Code.: 29333990
• Mol file: 1256388-51-8.mol

Synonyms:Methyl[(2S)-1-{(6S)-6-[5-(9,9-Difluoro-7-{2-[(1R,3S,4S)-2-{(2S)-2[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-azabicyclo[2.2.1]-hept-3-yl]-1H-benzimidazol-6-yl}-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-azaspiro[2.4]hept-5-yl}-3-methyl-1-oxobutan-2-yl]carba-mate

Chemical Property of Ledipasvir

Chemical Property:

• PKA: 11.20±0.10(Predicted)
• PSA: 174.64000
• Density: 1.42±0.1 g/cm3(Predicted)
• LogP: 9.26490
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly)

Purity/Quality:

98.0% ^*data from raw suppliers

Ledipasvir ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Description: Ledipasvir is a potent NS5A inhibitor that is approved for use in combination with sofosbuvir, a nucleotide inhibitor of viral polymerase, for the treatment of chronic hepatitis C virus genotype 1 infection. This combination was discovered and developed at Gilead Sciences and is marketed as the fixed combination with brand name of Harvoni.
• Uses: Ledipasvir is most commonly used in combination with sofosbuvir for treatment in chronic hepatitis C genotype 1 patients. It inhibits an important viral phosphoprotein, NS5A, which is involved in viral replication, assembly, and secretion.

Technology Process of Ledipasvir

There total 52 articles about Ledipasvir which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

C59H70F2N8O10 → methyl [(2S)-1-{(6S)-6-[5-(9,9-difluoro-7-{2-[(1R,3S,4S)-2-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-azabicyclo[2.2.1]-hept-3-yl]-1H-benzimidazol-6-yl}-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-azaspiro[2.4]hept-5-yl}-3-methyl-1-oxobutan-2-yl]carbamate (1256388-51-8)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; dichloromethane; at 10 ℃; for 5h;

Reference yield: 100.0%

C63H60Cl2F2N8O8 → methyl [(2S)-1-{(6S)-6-[5-(9,9-difluoro-7-{2-[(1R,3S,4S)-2-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-azabicyclo[2.2.1]-hept-3-yl]-1H-benzimidazol-6-yl}-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-azaspiro[2.4]hept-5-yl}-3-methyl-1-oxobutan-2-yl]carbamate (1256388-51-8)

Guidance literature:

With potassium phosphate; In tert-Amyl alcohol; water; at 90 ℃; for 5h;

Reference yield: 90.0%

(1-{6-[5-(7-bromo-9,9-difluoro-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-aza-spiro[2.4]heptane-5-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester (1256388-50-7) + methyl ((S)-3-methyl-1-oxo-1-((1R,3S,4S)-3-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazole-2-yl)-2-azabicyclo[2.2.1]heptan-2-yl)butan-2-yl)carbamate (1378387-87-1) → methyl [(2S)-1-{(6S)-6-[5-(9,9-difluoro-7-{2-[(1R,3S,4S)-2-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-azabicyclo[2.2.1]-hept-3-yl]-1H-benzimidazol-6-yl}-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-azaspiro[2.4]hept-5-yl}-3-methyl-1-oxobutan-2-yl]carbamate (1256388-51-8)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In tert-Amyl alcohol; water; at 90 ℃; for 16h; Inert atmosphere;

upstream raw materials:

3-[6-(9,9-difluoro-7-{2-[5-(2-methoxycarbonylamino-3-methyl-butyryl)-5-aza-spiro[2.4]hept-6-yl]-3H-imidazol-4-yl}-9H-fluoren-2-yl)-1H-benzoimidazol-2-yl]-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

N-methoxycarbonyl-L-valine

6-[5-(7-bromo-9,9-difluoro-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-aza-spiro[2.4]heptane-5-carboxylic acid benzyl ester

(1-{6-[5-(7-bromo-9,9-difluoro-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-aza-spiro[2.4]heptane-5-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester

Downstream raw materials:

(1-{3-[6-(9,9-difluoro-7-{2-[5-(2-methoxycarbonylamino-3-methyl-butyryl)-5-aza-spiro[2.4]hept-6-yl]-3H-imidazol-4-yl}-9H-fluoren-2-yl)-1H-benzoimidazol-2-yl]2-aza-bicyclo[2.2.1]heptane-2-carbonyl}-2-methyl-propyl)carbamicacid methyl ester D-tartrate salt

Refernces

• 1、 -. "Ledipasvir preparation method". . . Retrieved 2018/05/16.
• 2、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF LEDIPASVIR". . . Retrieved 2017/06/19.