Production Method 1

24424-99-5

1523541-83-4

928758-14-9

Reaction Conditions

1.1 Reagents: Sodium carbonate Solvents: 1,4-Dioxane ,  Water ;  12 h, 25 °C

Reference

Preparation peptidomimetics as antiviral agents with inhibitory activity against 3CL proteases

, World Intellectual Property Organization, , ,

Production Method 2

928758-14-9

Reaction Conditions

Reference

Preparation of linked bis-1H-imidazoles, bis-1H-benzimidazoles and analogs end-capped with amino acid or peptide derivatives as NS5A synergists and their anti-HCV synergist combinations with an NS5A-targeting compound

, World Intellectual Property Organization, , ,

Production Method 3

928758-14-9

Reaction Conditions

1.1 Reagents: Lithium hydroxide Solvents: Methanol ,  Tetrahydrofuran ,  Water ;  18 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 2, rt

Reference

Resensitizing daclatasvir-resistant hepatitis C variants by allosteric modulation of NS5A

Sun, Jin-Hua; O'Boyle, Donald R. II; Fridell, Robert A.; Langley, David R.; Wang, Chunfu; et al, Nature (London, 2015, 527(7577), 245-248

Production Method 4

24424-99-5

951789-77-8

928758-14-9

Reaction Conditions

1.1 Reagents: Lead tetraacetate Solvents: Methanol ,  Dichloromethane ;  0 - 5 °C; 10 min, 0 °C; 50 min, rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt
1.3 Reagents: Triethylamine ;  cooled; 20 h, rt
1.4 Reagents: Hydrochloric acid Solvents: Water ;  pH 2, cooled

Reference

Preparation of substituted azoles and their use as hepatitis C virus inhibitors

, United States, , ,

Production Method 5

24424-99-5

951789-77-8

928758-14-9

Reaction Conditions

1.1 Catalysts: Lead tetraacetate Solvents: Methanol ,  Dichloromethane ;  5 min, 0 - 5 °C; 10 min, 0 °C; 50 min, rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt
1.3 Reagents: Hydrochloric acid Solvents: Water ;  20 h, rt
1.4 Reagents: Triethylamine Solvents: Methanol ;  cooled
1.5 rt; 20 h, rt
1.6 Reagents: Hydrochloric acid Solvents: Water ;  pH 2, rt

Reference

Preparation of linked bis-1H-imidazoles, bis-1H-benzimidazoles and analogs end-capped with amino acid or peptide derivatives as NS5A synergists and their anti-HCV synergist combinations with an NS5A-targeting compound

, United States, , ,

Production Method 6

928758-14-9

Reaction Conditions

1.1 Reagents: Lithium hydroxide Solvents: Methanol ,  Tetrahydrofuran ,  Water ;  4 - 48 h, rt

Reference

Practical and efficient method for amino acid derivatives containing β-quaternary center: Application toward synthesis of hepatitis C virus NS3 serine protease inhibitors

Arasappan, Ashok; Venkatraman, Srikanth; Padilla, Angela I.; Wu, Wanli; Meng, Tao; et al, Tetrahedron Letters, 2007, 48(36), 6343-6347

(S)-2-((Tert-Butoxycarbonyl)amino)-2-(1-methylcyclopropyl)acetic acid Raw materials

• Di-tert-butyl dicarbonate
• Cyclopropaneacetonitrile, α-[[(1R)-2-hydroxy-1-phenylethyl]amino]-1-methyl-, (αS)-
• (2S)-2-Amino-2-(1-methylcyclopropyl)acetic acid hydrochloride

(S)-2-((Tert-Butoxycarbonyl)amino)-2-(1-methylcyclopropyl)acetic acid Preparation Products

• (S)-2-((Tert-Butoxycarbonyl)amino)-2-(1-methylcyclopropyl)acetic acid (928758-14-9)

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• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Amino acids and derivatives

Compound CAS No. 928758-14-9: (S)-2-((Tert-Butoxycarbonyl)amino)-2-(1-methylcyclopropyl)acetic Acid

The compound with CAS No. 928758-14-9, known as (S)-2-((Tert-Butoxycarbonyl)amino)-2-(1-methylcyclopropyl)acetic acid, is a highly specialized organic molecule that has garnered significant attention in the fields of organic chemistry and pharmaceutical research. This compound is notable for its unique stereochemistry and functional groups, which make it a valuable tool in the synthesis of complex molecules and potential drug candidates.

The tert-butoxycarbonyl (Boc) group is a well-known protecting group in peptide synthesis, playing a crucial role in controlling the reactivity of amino groups during multi-step syntheses. The presence of the Boc group in this compound underscores its utility in protecting the amine functionality while allowing for precise manipulation of the other parts of the molecule. This feature is particularly advantageous in the construction of bioactive compounds, where regioselectivity and stereoselectivity are paramount.

The 1-methylcyclopropyl substituent adds another layer of complexity to this molecule. Cyclopropane rings are known for their unique electronic and steric properties, which can significantly influence the reactivity and biological activity of a compound. The methyl substitution further modulates these properties, potentially enhancing the molecule's stability or bioavailability. Recent studies have highlighted the importance of such strained ring systems in drug design, particularly in targeting specific receptors or enzymes.

Acetic acid derivatives like this one are fundamental building blocks in organic synthesis. The acetic acid moiety provides a versatile platform for further functionalization, enabling chemists to introduce additional groups or modify existing ones to achieve desired properties. The stereochemistry at the central carbon atom, denoted by the (S) configuration, is critical for determining the molecule's interactions with biological systems. Stereoisomers often exhibit vastly different pharmacological profiles, making precise control over stereochemistry essential in drug development.

Recent advancements in asymmetric synthesis have revolutionized the production of enantiomerically pure compounds like (S)-2-((Tert-Butoxycarbonyl)amino)-2-(1-methylcyclopropyl)acetic acid. Techniques such as enzymatic resolution and chiral catalysis have enabled researchers to efficiently obtain the desired enantiomer with high optical purity. This capability is crucial for studying the compound's biological activity and ensuring its safety and efficacy in preclinical trials.

In terms of applications, this compound serves as an intermediate in the synthesis of more complex molecules, particularly those with potential therapeutic value. Its role as a precursor highlights its importance in medicinal chemistry pipelines, where it can be further modified to target specific diseases or conditions. For instance, derivatives of this compound have shown promise in inhibiting certain enzymes associated with neurodegenerative diseases, making it a valuable lead compound for drug discovery efforts.

Moreover, the integration of computational chemistry tools has provided deeper insights into the molecular properties of this compound. Advanced molecular modeling techniques allow researchers to predict its binding affinity to target proteins, optimize its pharmacokinetic profile, and design analogs with improved bioactivity. These computational approaches complement experimental studies, accelerating the discovery process and reducing costs associated with traditional trial-and-error methods.

In conclusion, (S)-2-((Tert-Butoxycarbonyl)amino)-2-(1-methylcyclopropyl)acetic acid represents a pivotal molecule in contemporary organic chemistry and pharmacology. Its unique structure, functional groups, and stereochemistry make it an invaluable asset in both academic research and industrial drug development. As scientific understanding continues to evolve, this compound will undoubtedly play an increasingly important role in advancing our ability to design and synthesize innovative therapeutic agents.

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• 54256-41-6(2-{[(tert-butoxy)carbonyl]amino}-2-cyclopropylacetic acid)
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