1335316-40-9

Basic information

• Product Name: (2S,5S)-1-((methoxycarbonyl)-L-valyl)-5-methylpyrrolidine-2-carboxylic acid
• Synonyms: (2S,5S)-1-((methoxycarbonyl)-L-valyl)-5-methylpyrrolidine-2-carboxylic acid;(2S,4S)-1-((R)-2-((methoxycarbonyl) amino)-2-phenylacetyl)-4-(methoxy methyl)pyrrolidine-2-carboxylic acid;(5S)-N-(Methoxycarbonyl)-L-valyl-5-methyl-L-proline;(2S,5S)-1-((S)-2-((methoxycarbonyl)amino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carboxylic acid;3. (2S,5S)-1-((S)-2-((methoxycarbonyl)amino)-3- methylbutanoyl)-5-methylpyrrolidine-2-carboxylic acid;(2S,5S)-1-((S)-2-(methoxycarbonyl)-3-methylbutanoyl);(2S,5S)-1-(2-Methoxycarbonylamino-3-methyl-butyryl)-5-methyl-pyrrolidine-2-carboxylic acid;N-[2-(S)-[(Methoxycarbonyl)amino]-3-methylbutyryl]-(5S)-5-Methyl-L-proline
• CAS NO: 1335316-40-9
• Molecular Formula: C₁₃H₂₂N₂O₅
• Molecular Weight: 286.33
• EINECS: 1312995-182-4
• Mol File: 1335316-40-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 489.9±40.0 °C(Predicted)
• Appearance: /
• Density: 1.198±0.06 g/cm3(Predicted)
• Storage Temp.: -20°C, Inert atmosphere
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 3.61±0.40(Predicted)
• CAS DataBase Reference: (2S,5S)-1-((methoxycarbonyl)-L-valyl)-5-methylpyrrolidine-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5S)-1-((methoxycarbonyl)-L-valyl)-5-methylpyrrolidine-2-carboxylic acid(1335316-40-9)
• EPA Substance Registry System: (2S,5S)-1-((methoxycarbonyl)-L-valyl)-5-methylpyrrolidine-2-carboxylic acid(1335316-40-9)

Safety Data

• Hazardous Substances Data: 1335316-40-9(Hazardous Substances Data)

Usage

Uses

(5S)-N-(Methoxycarbonyl)-L-valyl-5-methyl-L-proline is an antiviral agent and Velpatasvir (V116000) intermediate. Velpatasvir is a NS5A inhibitor in patients with hepatitis C (HCV) infection.

Synthesis

To an ice-cold stirred solution of ethyl (2S,5S)-1 -[(2S)-2- (methoxycarbonylamino)-3-methyl-butanoyl]-5-methyl-pyrrolidine-2- carboxylate (5.6 g, 17.8 mmol) in ethanol (18 ml) is added a solution of lithium hydroxide monohydrate (17.8 mL of 1.7 M, 30.3 mmol). The reaction mixture is stirred for 5 hours at rt. The reaction mixture is concentrated, diluted with water, washed with ether. The aqueous solution is acidified with aq. 1 N HCl, extracted with CH2CI2. The combined extracts are washed with brine, dried (Na2S04), concentrated to afford (2S,5S)-1 -[(2S)-2-(methoxycarbonylamino)-3- methyl-butanoyl]-5-methyl-pyrrolidine-2-carboxylic acid (5g, 94%) as a white solid.

Upstream product

• 111398-44-8 N-methoxycarbonyl-L-valine 
• 676560-84-2 (2S,5S)-5-methylpyrrolidine-2-carboxylic acid ethyl ester 
• 676560-83-1 (2S,5S)-5-methyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 913251-58-8 (S)-2-(tert-butoxycarbonylamino)-5-oxohexanoic acid ethyl ester 
• 144978-35-8 (S)-ethyl N-tert-butoxycarbonylpyroglutamate 
• 676560-85-3 (2S,5S)-ethyl 5-methylpyrrolidine-2-carboxylate 2,2,2-trifluoro acetate salt 
• 1335316-39-6 (2S,5S)-ethyl 1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carboxylate 
• 72-18-4 L-valine 

Downstream Products

• 1335316-35-2 tert-butyl (2S,5S)-2-[4-[4-[4-[2-[(2S,5S)-1-[2-(methoxycarbonylamino)-3-methyl-butanoyl]-5-methyl-pyrrolidin-2-yl]-1H-benzimidazol-5-yl]phenyl]phenyl]-1H-imidazol-2-yl]-5-methyl-pyrrolidine-1-carboxylate 
• 1335316-38-5 methyl N-[2-methyl-1-[(2S,5S)-2-methyl-5-[4-[4-[4-[2-[(2S,5S)-5-methylpyrrolidin-2-yl]-1H-imidazol-5-yl]phenyl]phenyl]-1H-benzimidazol-2-yl]pyrrolidine-1-carbonyl]propyl]-carbamate 
• 1335315-74-6 methyl N-[(1S)-1-[(2S,5S)-2-[4-[4-[4-[2-[(2S,5S)-1-[2-(methoxycarbonylamino)-3-methyl-butanoyl]-5-methyl-pyrrolidin-2-yl]-1H-benzimidazol-5-yl]phenyl]phenyl]-1H-imidazol-2-yl]-5-methyl-pyrrolidine-1-carbonyl]-2-methyl-propyl]carbamate 
• 1378391-43-5 (2R,4R)-1-tert-butyl 2-(2-(9-((2S,5S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carbonyloxy)-8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)-2-oxoethyl) 4-(methoxymethyl)pyrrolidine-1,2-dicarboxylate 

Relevant articles and documents

Compounds for inhibiting HCV (hepatitis C virus), pharmaceutical composition and application of compounds or pharmaceutical composition

The invention discloses compounds for inhibiting HCV (hepatitis C virus), pharmaceutical composition and an application of the compounds or the pharmaceutical composition. The compounds are compoundsshown in formula (I) or a stereoisomer, geometric isomer, a tautomer, an enantiomer, sulfur oxide, nitrogen oxide, hydrate, solvate, metabolite, pharmaceutically acceptable salt or prodrug of the compounds shown in formula (I); the compounds are effective antiviral drugs, especially can be used for inhibiting the function of NS5A protein encoded by the HCV, thereby effectively inhibiting the HCV.The method for preventing and/or treating drugs or diseases associated with the HCV by the compounds or the composition containing the new compounds has good market development prospects.

ANTIVIRAL COMPOUNDS

The disclosure is related to anti-viral compounds, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.

CONDENSED IMIDAZOLYLIMIDAZOLES AS ANTIVIRAL COMPOUNDS

The disclosure is related to anti-viral compounds, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.