74761-42-5

Basic information

• Product Name: (S)-2-((Methoxycarbonyl)aMino)-3-Methylbutanoic acid
• Synonyms: (S)-2-((Methoxycarbonyl)aMino)-3-Methylbutanoic acid;MOC-L-Valine;N-(Methoxycarbonyl)-L-valine;L-Valine, N-(Methoxycarbonyl)-;Moc-Val-OH;(2S)-2-[(Methoxycarbonyl)aMino]-3-Methylbutanoic acid;N-(methoxycarbonyl)-Valine;MOC-L-Val
• CAS NO: 74761-42-5
• Molecular Formula: C₇H₁₃NO₄
• Molecular Weight: 175.18242
• Product Categories: Pharmaceuticalintermediates
• Mol File: 74761-42-5.mol
• Article Data: 83

Chemical Properties

• Melting Point: 109.0 to 113.0 °C
• Boiling Point: 315.9±25.0 °C(Predicted)
• Appearance: /
• Density: 1.154±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.44±0.10(Predicted)
• CAS DataBase Reference: (S)-2-((Methoxycarbonyl)aMino)-3-Methylbutanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-((Methoxycarbonyl)aMino)-3-Methylbutanoic acid(74761-42-5)
• EPA Substance Registry System: (S)-2-((Methoxycarbonyl)aMino)-3-Methylbutanoic acid(74761-42-5)

Safety Data

• Hazardous Substances Data: 74761-42-5(Hazardous Substances Data)

Usage

Description

(S)-2-((Methoxycarbonyl)aMino)-3-Methylbutanoic acid is a chiral compound that serves as an intermediate in the synthesis of pharmaceuticals and other organic compounds. It is characterized by its unique stereochemistry, which is crucial for its reactivity and potential applications in various chemical processes.

Uses

Used in Pharmaceutical Industry:
(S)-2-((Methoxycarbonyl)aMino)-3-Methylbutanoic acid is used as a Ledipasvir Intermediate for the development of antiviral medications, specifically targeting hepatitis C virus (HCV) infections. Its role in the synthesis of Ledipasvir contributes to the drug's efficacy in treating HCV by inhibiting the viral NS5A protein, thereby suppressing viral replication and assembly.
Used in Laboratory Research and Development:
(S)-2-((Methoxycarbonyl)aMino)-3-Methylbutanoic acid is utilized in laboratory settings for the synthesis and study of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique properties and reactivity make it a valuable tool for researchers in the development of new chemical entities and processes.
Used in Chemical Production Process:
(S)-2-((Methoxycarbonyl)aMino)-3-Methylbutanoic acid is employed in the chemical production process to synthesize a range of products, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its versatility and reactivity in various chemical reactions make it an essential component in the manufacturing of these products.

Synthesis

Na2CO3 (1.83 g, 17.2 mmol) was added to an aq solution of NaOH (33 mL of 1 M/H2O, 33 mmol) and L-valine (3.900 g, 33.29 mmol) and the resulting solution was cooled with ice-water bath. Methyl chloroformate (2.8 mL, 36.1 mmol) was added dropwise, the cooling bath was removed and the reaction mixture was stirred at ambient temperature for 3.25 h. The reaction mixture was washed with ether (3x17 mL), and the aqueous phase was cooled with ice-water bath and acidified with conc HCl to a pH of 1-2, and extracted with CH2Cl2 (3x17 mL). The organic phase was dried (anhyd MgSO4), filtered, and concentrated in vacuo. Cap-1 as a white solid (5.00 g, 86%).

Upstream product

• 63-91-2 L-phenylalanine 
• 98807-38-6 Z-L-Val-O-COOMe 
• 72-18-4 L-valine 
• 79-22-1 methyl chloroformate 
• 17498-50-9 L-valine hydrochloride 
• 1208007-67-3 1,1-dimethylethyl (2S)-2-(5-bromo-1H-benzimidazol-2-yl)-1-pyrrolidinecarboxylate 
• 13518-40-6 L-valine tert-butylester hydrochloride 
• 112175-14-1 Moc-L-Val-O-COOMe 

Downstream Products

• 180462-96-8 N'-Cyclohexylmethyl-N'-[(2S,3S)-2-hydroxy-3-((S)-2-methoxycarbonylamino-3-methyl-butyrylamino)-4-phenyl-butyl]-hydrazinecarboxylic acid tert-butyl ester 
• 161968-14-5 1-[2(S)-hydroxy-3(S)-(N-(methoxycarbonyl)-(L)-valyl)amino-4-phenyl-butyl]-1-[cyclohexylmethyl]-2-[N-methoxycarbonyl-(L)-valyl]-hydrazine 
• 872703-55-4 [(1S)-1-(N'-benzyl-hydrazinocarbonyl)-2-methyl-propyl]carbamic acid methyl ester 
• 1007885-17-7 4,4'-bis(2-((2S)-1-(N-(methoxycarbonyl)-L-valyl)-2-pyrrolidinyl)-1H-imidazol-5-yl)-2-biphenylcarboxylic acid 
• 202586-01-4 1-[p-(N,N-diethylamino)phenyl]-4(S)-hydroxy-2-[N-(N-methoxycarbonyl-(L)-valyl)amino]-5(S)-[N-(N-methoxycarbonyl-(L)-tert-leucyl)amino]-6-phenyl-2-azahexane 
• 202586-06-9 1-[p-(pyrrolidin-1-yl)phenyl]-4(S)-hydroxy-2-[N-(N-methoxycarbonyl-(L)-valyl)amino]-5(S)-[N-(N-methoxycarbonyl-(L)-tert-leucyl)amino]-6-phenyl-2-azahexane 
• 202586-34-3 1-[p-(Pyrrolidin-1-yl)phenyl]-4(S)-hydroxy-2-(tert-butyloxycarbonyl)amino-5(S)-[N-(N-methoxycarbonyl-(L)-valyl)amino]-6-phenyl-2-azahexane 
• 202586-11-6 1-[p-(pyrrolidin-1-yl)phenyl]-4(S)-hydroxy-2-[N-(N-methoxycarbonyl-(L)-valyl)amino]-5(S)-[N-(N-methoxycarbonyl-(L)-isoleucyl)amino]-6-phenyl-2-azahexane 
• 202586-43-4 1-[p-(1,2,4-Triazol-4-yl)phenyl]-4(S)-hydroxy-2-(tert-butyloxycarbonyl)amino-5(S)[N-(N-methoxycarbonyl-(L)-valyl)amino]-6-phenyl-2-azahexane 
• 202586-49-0 1-[p-(1,2,4-Triazol-1-yl)phenyl]-4(S)-hydroxy-2-(tert-butyloxycarbonyl)amino-5(S)-[N-(N-methoxycarbonyl-(L)-valyl)amino]-6-phenyl-2-azahexane 
• 202586-14-9 1-[p-(4-methylpiperazin-1-yl)phenyl]-4(S)-hydroxy-5(S)-2,5-bis[N-(N-methoxycarbonyl-(L)-valyl)amino]-6-phenyl-2-azahexane 
• 202586-55-8 1-[p-(4-methylpiperazin-1-yl)phenyl]-4(S)-hydroxy-2-(tert-butyloxycarbonyl)amino-5(S)-[N-(N-methoxycarbonyl-(L)-valyl)amino]-6-phenyl-2-azahexane 
• 198904-22-2 1-[4-(Pyridin-2-yl)-phenyl]-4(S)-hydroxy-5(S)-2,5-bis[N-(N-methoxycarbonyl-(L)-valyl)amino]-6-phenyl-2-azahexane 
• 198904-05-1 1-[4-(Thiazol-2-yl)-phenyl]-4(S)-hydroxy-5(S)-2,5-bis[N-(N-methoxycarbonyl-(L)-valyl)amino]-6-phenyl-2-azahexane 

Relevant articles and documents

Redesigning of the cap conformation and symmetry of the diphenylethyne core to yield highly potent pan-genotypic NS5A inhibitors with high potency and high resistance barrier

Herein, we report the discovery of several NS5A inhibitors with potency against HCV genotype 1b in the picomolar range. Compounds (15, 33) were of extremely high potency against HCV genotype 1b (EC50 ≈ 1 pM), improved activity against genotype 3a (GT 3a) and good metabolic stability. We studied the impact of changing the cap conformation relative to the diphenylethyne core and/or compound symmetry on both potency and metabolic stability. The analogs obtained exhibited improved potency against HCV genotypes 1a, 1b, 3a and 4a compared to the clinically approved candidate daclatasvir with EC50 values in the low picomolar range and SI50s > 7 orders of magnitude. Compound 15, a symmetrically m-, m’-substituted diphenyl ethyne analog, was 150-fold more potent than daclatasvir against GT 3a, while compound 33, an asymmetrically m-, p-substituted diphenyl ethyne analog, was 35-fold more potent than daclatasvir against GT 3a. In addition, compound 15 exhibited a higher resistance barrier than daclatasvir against genotype 1b.

Design and synthesis of novel symmetric fluorene-2,7-diamine derivatives as potent hepatitis C virus inhibitors

Hepatitis C virus (HCV) is an international challenge. Since the discovery of NS5A direct-acting antivirals, researchers turned their attention to pursue novel NS5A inhibitors with optimized design and structure. Herein we explore highly potent hepatitis C virus (HCV) NS5A inhibitors; the novel analogs share a common symmetrical prolinamide 2,7-diaminofluorene scaffold. Modification of the 2,7-diaminofluorene backbone included the use of (S)-prolinamide or its isostere (S,R)-piperidine-3-caboxamide, both bearing different amino acid residues with terminal carbamate groups. Compound 26 exhibited potent inhibitory activity against HCV genotype (GT) 1b (effective concentration (EC50) = 36 pM and a selectivity index of >2.78 × 106). Compound 26 showed high selectivity on GT 1b versus GT 4a. Interestingly, it showed a significant antiviral effect against GT 3a (EC50 = 1.2 nM). The structure-activity relationship (SAR) analysis revealed that picomolar inhibitory activity was attained with the use of S-prolinamide capped with R- isoleucine or R-phenylglycine residues bearing a terminal alkyl carbamate group.

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.