401909-61-3

Basic information

• Product Name: 1H-Pyrrole-2-carboxylic acid, 2,5-dihydro-3-[[(trifluoromethyl)sulfonyl]oxy]-1-(triphenylmethyl)-, methyl ester, (2S)-
• CAS NO: 401909-61-3
• Molecular Formula: C26H22F3NO5S
• Molecular Weight: 517.526
• Mol File: 401909-61-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1H-Pyrrole-2-carboxylic acid, 2,5-dihydro-3-[[(trifluoromethyl)sulfonyl]oxy]-1-(triphenylmethyl)-, methyl ester, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrole-2-carboxylic acid, 2,5-dihydro-3-[[(trifluoromethyl)sulfonyl]oxy]-1-(triphenylmethyl)-, methyl ester, (2S)-(401909-61-3)
• EPA Substance Registry System: 1H-Pyrrole-2-carboxylic acid, 2,5-dihydro-3-[[(trifluoromethyl)sulfonyl]oxy]-1-(triphenylmethyl)-, methyl ester, (2S)-(401909-61-3)

Safety Data

• Hazardous Substances Data: 401909-61-3(Hazardous Substances Data)

Usage

Molecular structure

1H-Pyrrole-2-carboxylic acid, 2,5-dihydro-3-[[(trifluoromethyl)sulfonyl]oxy]-1-(triphenylmethyl)-, methyl ester, (2S)is a complex organic molecule that consists of a pyrrole ring, a carboxylic acid group, a methyl ester group, a trifluoromethylsulfonyl group, and a triphenylmethyl group.

Derivative

This chemical is a methyl ester derivative of 1H-pyrrole-2-carboxylic acid, which means that a methyl ester group has been added to the parent compound.

Trifluoromethylsulfonyl group

The presence of a trifluoromethylsulfonyl group gives this chemical a specific chemical and physical properties, such as increased lipophilicity, which can enhance its ability to cross cell membranes and interact with biological targets.

Triphenylmethyl group

The presence of a triphenylmethyl group gives this chemical a specific chemical and physical properties, such as increased stability and resistance to degradation, which can enhance its pharmacokinetic properties.

(2S)configuration

This chemical exists in the (2S)configuration, which refers to the arrangement of the atoms in space and can have a significant impact on the chemical's biological activity and pharmacokinetic properties.

Pharmaceutical research and drug development

This chemical is often used in pharmaceutical research and drug development due to its potential as a bioactive compound.

Applications

It may have applications in the treatment of various diseases and conditions, and its specific properties and potential effects are subjects of ongoing study and investigation.

Complex structure

The complex structure of this chemical, with multiple functional groups and a specific configuration, can give it a range of chemical and biological properties that can be harnessed for various applications in the field of medicine.

Upstream product

• 145100-51-2 N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide 
• 401909-59-9 (S)-3-Oxo-1-trityl-pyrrolidine-2-carboxylic acid methyl ester 
• 76-83-5 trityl chloride 
• 401909-57-7 (2S,3S)-1-(triphenylmethyl)-3-hydroxyproline methyl ester 
• 496841-04-4 methyl (2S,3S)-3-hydroxypyrrolidine-2-carboxylate 
• 4298-08-2 trans-3-hydroxy-L-proline 

Downstream Products

• 401909-65-7 3-phenyl-1-trityl-2,5-dihydro-1H-pyrrole-2-carboxylic acid methyl ester 
• 1104070-76-9 (S)-methyl 3-(4-(trifluoromethyl)phenyl)-1-trityl-2,5-dihydro-1H-pyrrole-2-carboxylate 
• 401909-77-1 3-methyl-1-trityl-2,5-dihydro-1H-pyrrole-2-carboxylic acid methyl ester 
• 401909-81-7 1-trityl-2,5-dihydro-1H-pyrrole-2,3-dicarboxylic acid dimethyl ester 

Relevant articles and documents

Discovery of the pan-genotypic hepatitis C virus NS3/4A protease inhibitor voxilaprevir (GS-9857): A component of Vosevi

Treatment of hepatitis C virus (HCV) infection has been historically challenging due the high viral genetic complexity wherein there are eight distinct genotypes and at least 86 viral subtypes. While HCV NS3/4A protease inhibitors are an established treatment option for genotype 1 infection, limited coverage of genotypes 2 and/or 3 combined with serum alanine transaminase (ALT) elevations for some compounds has limited the broad utility of this therapeutic class. Our discovery efforts were focused on identifying an NS3/4A protease inhibitor with pan-genotypic antiviral activity, improved coverage of resistance associated substitutions, and a decreased risk of hepatotoxicity. Towards this goal, distinct interactions with the conserved catalytic triad of the NS3/4A protease were identified that improved genotype 3 antiviral activity. We further discovered that protein adduct formation strongly correlated with clinical ALT elevation for this therapeutic class. Improving metabolic stability and decreasing protein adduct formation through structural modifications ultimately resulted in voxilaprevir. Voxilaprevir, in combination with sofosbuvir and velpatasvir, has demonstrated pan-genotypic antiviral clinical activity. Furthermore, hepatotoxicity was not observed in Phase 3 clinical trials with voxilaprevir, consistent with our design strategy. Vosevi (sofosbuvir, velpatasvir, and voxilaprevir) is now an approved pan-genotypic treatment option for the most difficult-to-cure individuals who have previously failed direct acting antiviral therapy.

Enantioselective approach to 3-substituted prolines

Enantioselective synthesis of 3-substituted prolines was achieved starting from commercially available 3-hydroxy-(S)-2-proline. Palladium-mediated couplings were used to introduce a variety of groups at C3 using the corresponding enol triflate derived from N-trityl 3-oxo-(S)-2-proline methyl ester. Cleavage of the trityl residue and hydrogenation provided final products with good to modest diastereoselectivity.