Production Method 1

142-73-4

85916-13-8

Reaction Conditions

1.1 Reagents: Perchloric acid Solvents: tert-Butanol ,  tert-Butyl acetate

Reference

Synthesis of 4-(phenylethynyl)-2,6-bis[N,N-bis(carboxymethyl)aminomethyl]pyridine

Takalo, Harri; et al, Acta Chemica Scandinavica, 1988, 42(6), 373-7

Production Method 2

275371-57-8

85916-13-8

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  4 h, rt

Reference

A new generation of cross-linkers for selective detection by MALDI MS

Paramelle, David; et al, Proteomics, 2009, 9(23), 5384-5388

Production Method 3

85916-13-8

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  3 h, 45 °C
2.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  4 h, rt

Reference

A new generation of cross-linkers for selective detection by MALDI MS

Paramelle, David; et al, Proteomics, 2009, 9(23), 5384-5388

DL-tert-Butyl Iminodiacetate Raw materials

• N-Bis(tert-butylacetate) bnezylamine
• Iminodiacetic acid

DL-tert-Butyl Iminodiacetate Preparation Products

• DL-tert-Butyl Iminodiacetate (85916-13-8)

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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
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Recent Advances in the Application of DL-tert-Butyl Iminodiacetate (CAS: 85916-13-8) in Chemical Biology and Pharmaceutical Research

DL-tert-Butyl Iminodiacetate (CAS: 85916-13-8) is a versatile chemical compound that has garnered significant attention in the field of chemical biology and pharmaceutical research. This compound, characterized by its iminodiacetate moiety and tert-butyl ester groups, serves as a crucial intermediate in the synthesis of various biologically active molecules. Recent studies have highlighted its potential in drug discovery, peptide synthesis, and as a ligand in metal-catalyzed reactions. This research brief aims to provide an overview of the latest advancements and applications of DL-tert-Butyl Iminodiacetate, focusing on its role in modern pharmaceutical development.

One of the most notable applications of DL-tert-Butyl Iminodiacetate is its use as a building block in the synthesis of peptide-based therapeutics. Researchers have demonstrated its efficacy in facilitating the formation of stable peptide bonds, particularly in the context of constrained peptides. A recent study published in the Journal of Medicinal Chemistry showcased the compound's utility in the synthesis of cyclic peptides, which are increasingly being explored for their enhanced metabolic stability and target specificity. The study reported that DL-tert-Butyl Iminodiacetate significantly improved the yield and purity of the final peptide products, making it a valuable tool for peptide chemists.

In addition to its role in peptide synthesis, DL-tert-Butyl Iminodiacetate has been investigated for its potential as a ligand in metal-catalyzed reactions. A 2023 study in Advanced Synthesis & Catalysis explored its use in palladium-catalyzed cross-coupling reactions, which are fundamental to the construction of complex organic molecules. The researchers found that the compound's iminodiacetate moiety effectively coordinates with palladium, enhancing the reaction's efficiency and selectivity. This discovery opens new avenues for the development of more sustainable and cost-effective catalytic systems in pharmaceutical manufacturing.

Another emerging area of research involves the application of DL-tert-Butyl Iminodiacetate in the design of prodrugs. Prodrugs are biologically inactive compounds that undergo enzymatic or chemical transformation in vivo to release the active drug. A recent preprint on bioRxiv detailed the use of DL-tert-Butyl Iminodiacetate as a promoiety in the development of prodrugs for poorly soluble anticancer agents. The study reported that the incorporation of this compound improved the solubility and bioavailability of the prodrugs, thereby enhancing their therapeutic efficacy. These findings underscore the compound's potential in addressing one of the major challenges in drug delivery.

Despite its promising applications, the synthesis and handling of DL-tert-Butyl Iminodiacetate present certain challenges. A 2022 review in Organic Process Research & Development highlighted the need for optimized synthetic protocols to improve the scalability and cost-effectiveness of its production. The review also discussed the importance of developing greener synthetic routes, given the increasing emphasis on sustainable chemistry in the pharmaceutical industry. Future research directions may focus on addressing these challenges to fully harness the compound's potential.

In conclusion, DL-tert-Butyl Iminodiacetate (CAS: 85916-13-8) represents a valuable tool in chemical biology and pharmaceutical research, with diverse applications ranging from peptide synthesis to prodrug design. Recent studies have demonstrated its efficacy in improving reaction yields, enhancing drug solubility, and facilitating the development of novel therapeutic agents. As research in this area continues to evolve, further exploration of its synthetic and functional properties will be essential to unlocking its full potential. This brief underscores the importance of ongoing innovation and collaboration in the field to advance the applications of this versatile compound.

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