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

Uses

(S)-2-((Methoxycarbonyl)aMino)-3-Methylbutanoic acid can be used as Ledipasvir Intermediate, mainly used in laboratory R&D process and chemical production process.

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

• 17498-50-9 L-valine hydrochloride 
• 79-22-1 methyl chloroformate 
• 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 
• 63-91-2 L-phenylalanine 
• 98807-38-6 Z-L-Val-O-COOMe 
• 72-18-4 L-valine 

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 
• 191594-68-0 N'-Biphenyl-4-ylmethyl-N'-[(2S,3S)-2-hydroxy-3-((S)-2-methoxycarbonylamino-3-methyl-butyrylamino)-4-phenyl-butyl]-hydrazinecarboxylic acid tert-butyl ester 
• 198905-15-6 N'-[(2S,3S)-2-Hydroxy-3-((S)-2-methoxycarbonylamino-3-methyl-butyrylamino)-4-phenyl-butyl]-N'-(4-pyridin-2-yl-benzyl)-hydrazinecarboxylic acid tert-butyl ester 
• 198904-60-8 N'-[(2S,3S)-2-Hydroxy-3-((S)-2-methoxycarbonylamino-3-methyl-butyrylamino)-4-phenyl-butyl]-N'-(4-thiazol-2-yl-benzyl)-hydrazinecarboxylic acid tert-butyl ester 
• 198904-49-3 N'-[(2S,3S)-2-Hydroxy-3-((S)-2-methoxycarbonylamino-3-methyl-butyrylamino)-4-phenyl-butyl]-N'-(4-thiazol-5-yl-benzyl)-hydrazinecarboxylic acid tert-butyl ester 
• 198903-87-6 ((S)-1-{(1S,2S)-1-Benzyl-2-hydroxy-3-[N'-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-N-(4-thiazol-5-yl-benzyl)-hydrazino]-propylcarbamoyl}-2,2-dimethyl-propyl)-carbamic acid methyl ester 
• 198903-86-5 1-[4-(Thiazol-5-yl)-phenyl]-4(S)-hydroxy-5(S)-2,5-bis[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 
• 1007885-17-7 4,4'-bis(2-((2S)-1-(N-(methoxycarbonyl)-L-valyl)-2-pyrrolidinyl)-1H-imidazol-5-yl)-2-biphenylcarboxylic acid 
• 1246852-24-3 methyl ((1S)-1-(((2S)-2-(4-(4'-(2-((2S)-1-((2S)-2-((methoxycarbonyl)amino)-3-methylbutanoyl)-2-pyrrolidinyl)-1H-imidazol-4-yl)-1,1'-bi(3-cyclohexen-1-yl)-4-yl)-1H-imidazol-2-yl)-1-pyrrolidinyl)carbonyl)-2-methylpropyl)carbamate 
• 1261070-45-4 methyl {(2S)-1-[(2S)-2-{5-[4-(4-cyano-6-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}pyrrolidin-2-yl]-1H-imidazol-4-yl}quinolin-2-yl)phenyl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate 
• 1228552-83-7 [(S)-1-((S)-2-{5-[4-(6-{2-[(S)-1-((S)-2-methoxycarbonylamino-3-methylbutyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-quinazolin-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]carbamic acid methyl ester 
• 1261070-40-9 methyl {(2S)-1-[(2S)-2-{4-[4-(3-hydroxy-6-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}pyrrolidin-2-yl]-1H-imidazol-4-yl}quinoxalin-2-yl)phenyl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate 

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.