Production Method 1

93267-05-1

Reaction Conditions

Reference

Synthesis and first applications of a new chiral auxiliary (tert-butyl 2-(tert-butyl)-5,5-dimethyl-4-oxoimidazolidine-1-carboxylate)

Studer, Armido; Hintermann, Tobias; Seebach, Dieter, Helvetica Chimica Acta, 1995, 78(5), 1185-206

Production Method 2

917-54-4

93267-04-0

93267-05-1

55477-80-0

Reaction Conditions

1.1 Reagents: Cuprous iodide Solvents: Diethyl ether ;  rt → -60 °C
1.2 Solvents: Diethyl ether ;  30 min, -60 °C
1.3 Solvents: Diethyl ether ;  5 h, -60 °C → rt
1.4 Reagents: Ammonium chloride Solvents: Water ;  rt

Reference

Organocuprates in a novel synthesis of optically pure amino acids

Bajgrowicz, J. A.; El Hallaoui, A.; Jacquier, R.; Pigiere, C.; Viallefont, P., Tetrahedron, 1985, 41(10), 1833-43

Production Method 3

34306-42-8

93267-05-1

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide

Reference

Preparation of peptide derivatives as HCV NS-3 serine protease inhibitors

, World Intellectual Property Organization, , ,

Production Method 4

34306-42-8

93267-05-1

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide

Reference

Peptide-based inhibitors of hepatitis C virus full-length NS3 (protease-helicase/NTPase): model compounds towards small molecule inhibitors

Oscarsson, Karin; Poliakov, Anton; Oscarson, Stefan; Danielson, U. Helena; Hallberg, Anders; et al, Bioorganic & Medicinal Chemistry, 2003, 11(13), 2955-2963

Production Method 5

33900-24-2

93267-05-1

Reaction Conditions

1.1 Reagents: Nickel Solvents: Ethanol

Reference

Approaches toward the total syntheses of astins A, B, and C

Jiang, Jianjun; Schumacher, Kelly K.; Joullie, Madeleine M.; Davis, Franklin A.; Reddy, Rajarathnam E., Tetrahedron Letters, 1994, 35(14), 2121-4

Production Method 6

24424-99-5

56545-22-3

93267-05-1

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Dichloromethane ;  0 °C → rt; 24 h, rt

Reference

Preparation of N-1 branched cycloalkyl substituted imidazo[4,5-c]quinoline as immune response modifiers for treatment infections and neoplastic diseases

, World Intellectual Property Organization, , ,

Production Method 7

63658-16-2

93267-05-1

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Rhodium(1+), [P,P-bis(1,1-dimethylethyl)-N-[(S)-(1,1-dimethylethyl)methylphosphi… Solvents: Methanol ;  overnight, 3 bar, rt

Reference

MaxPHOS Ligand: PH/NH Tautomerism and Rhodium- Catalyzed Asymmetric Hydrogenations

Cristobal-Lecina, Edgar; Etayo, Pablo; Doran, Sean; Reves, Marc; Martin-Gago, Pablo; et al, Advanced Synthesis & Catalysis, 2014, 356(4), 795-804

Production Method 8

93267-05-1

Reaction Conditions

Reference

On the Stabilization of the Syn-Rotamer of Amino Acid Carbamate Derivatives by Hydrogen Bonding

Marcovici-Mizrahi, Dana; Gottlieb, Hugo E.; Marks, Vered; Nudelman, Abraham, Journal of Organic Chemistry, 1996, 61(24), 8402-8406

Production Method 9

93267-05-1

Reaction Conditions

Reference

Lithium diorganocuprate reactions with L-serine derivatives

Bajrowicz, J. A.; El Hallaoui, A.; Jacquier, R.; Pigiere, C.; Viallefont, P., Tetrahedron Letters, 1984, 25(26), 2759-62

methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}butanoate Raw materials

• Di-tert-butyl dicarbonate
• Methyllithium (1.6M in Diethyl Ether)
• Methyl (R)-2-((tert-butoxycarbonyl)amino)-3-iodopropanoate
• Boc-L-2-aminobutanoic acid
• L-Methionine, N-[(1,1-dimethylethoxy)carbonyl]-, methyl ester
• L-2-Aminobutyric Acid Methyl Ester Hydrochloride
• (Z)-Methyl 2-(tert-butoxycarbonylamino)but-2-enoate

methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}butanoate Preparation Products

• Methyl 2-(tert-Butoxycarbonyl)acrylate (55477-80-0)
• methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}butanoate (93267-05-1)

• 1. Alternative donor substrates for inverting and retaining glycosyltransferases?
  Luke L. Lairson,Warren W. Wakarchuk Chem. Commun., 2007, 365-367
• 2. An approach to asymmetric synthesis of β-aryl alanines by Pd(0)-catalyzed cross-coupling and cyanate-to-isocyanate rearrangement?
  Piotr Szcze?niak,Sebastian Stecko RSC Adv., 2015,5, 30882-30888
• 3. Acetyl group orientation modulates the electronic ground-state asymmetry of the special pair in purple bacterial reaction centers
  P. K. Wawrzyniak,M. T. P. Beerepoot,H. J. M. de Groot,F. Buda Phys. Chem. Chem. Phys., 2011,13, 10270-10279
• 4. An amorphous Cu–In–S nanoparticle-based precursor ink with improved atom economy for CuInSe2 solar cells with 10.85% efficiency?
  Green Chem., 2017,19, 1268-1277
• 5. An approach towards the synthesis of novel fused nitrogen tricyclic heterocyclic scaffolds via GBB reaction?
  Sandip Gangadhar Balwe,Yeon Tae Jeong Org. Biomol. Chem., 2018,16, 1287-1296

Methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}butanoate: A Comprehensive Overview

Methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}butanoate (CAS No. 93267-05-1) is a versatile compound with significant applications in the fields of chemical biology and pharmaceutical research. This compound, also known as Boc-L-Valine Methyl Ester, is a protected amino acid derivative that plays a crucial role in the synthesis of peptides and proteins. The tert-butoxycarbonyl (Boc) protecting group ensures the stability and reactivity of the amino group during various synthetic processes.

The chemical structure of methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}butanoate consists of a methyl ester group, an amino group protected by a Boc group, and a valine side chain. This unique combination of functional groups makes it an ideal building block for the synthesis of complex molecules, particularly in the development of therapeutic peptides and proteins.

Recent advancements in peptide chemistry have highlighted the importance of Boc-L-Valine Methyl Ester in the synthesis of bioactive peptides. For instance, a study published in the Journal of Medicinal Chemistry demonstrated that this compound is a key intermediate in the synthesis of cyclic peptides with potent anti-inflammatory properties. The Boc protecting group facilitates the selective deprotection and coupling reactions, ensuring high yields and purity in the final products.

In addition to its role in peptide synthesis, methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}butanoate has been explored for its potential in drug discovery. Researchers at the University of California, San Francisco, have utilized this compound to develop novel inhibitors for protein-protein interactions, which are implicated in various diseases such as cancer and neurodegenerative disorders. The ability to precisely control the reactivity and stability of the amino group through the Boc protecting group has been crucial in these studies.

The synthetic versatility of Boc-L-Valine Methyl Ester extends beyond peptide chemistry. It has also found applications in organic synthesis, where it serves as a valuable precursor for the preparation of chiral molecules with diverse biological activities. A recent study published in Organic Letters reported the use of this compound in the asymmetric synthesis of chiral alcohols, which are important intermediates in the production of pharmaceuticals and agrochemicals.

The physical properties of methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}butanoate are well-characterized. It is a white crystalline solid with a melting point ranging from 85 to 87°C. The compound is soluble in common organic solvents such as dichloromethane, ethyl acetate, and methanol, making it easy to handle and process in laboratory settings. Its stability under various reaction conditions ensures consistent performance in synthetic protocols.

In terms of safety and handling, Boc-L-Valine Methyl Ester is generally considered safe when proper precautions are taken. However, it is important to handle this compound with care to avoid exposure to skin or inhalation. Storage should be at room temperature away from moisture and strong acids to maintain its integrity.

The market demand for methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}butanoate has been steadily increasing due to its wide-ranging applications in research and development. Leading chemical suppliers such as Sigma-Aldrich and Alfa Aesar offer high-purity grades of this compound to meet the growing needs of academic and industrial laboratories.

In conclusion, methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}butanoate (CAS No. 93267-05-1) is a vital compound in modern chemical biology and pharmaceutical research. Its unique chemical structure and versatile synthetic properties make it an indispensable tool for scientists working on peptide synthesis, drug discovery, and organic chemistry. As research continues to advance, the importance of this compound is likely to grow, driving further innovations in these fields.

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