58948-98-4

Usage

Uses

Used in Chemical Synthesis:
Isocyanoacetic acid potassium salt is used as a reagent for carbene insertion reactions, serving as a cleanup procedure to remove ruthenium carbene catalysts from metathesis reaction products. This application is crucial in ensuring the purity of the final product and preventing unwanted side reactions.
Used in Organometallic Chemistry:
In the field of organometallic chemistry, isocyanoacetic acid potassium salt is utilized for the preparation of carbonyl complexes of group IVB metals. These complexes are important intermediates in various chemical processes and can be used to synthesize a wide range of compounds.
Used in Peptide Synthesis:
Isocyanoacetic acid potassium salt is also employed in the preparation of peptides via the ammonium chloride-promoted Ugi reaction. This multicomponent reaction is a powerful tool in the synthesis of peptide-based compounds, allowing for the rapid assembly of complex molecules from simpler precursors.

Upstream product

• 2999-46-4 Ethyl isocyanoacetate 
• 39687-95-1 isocyanoacetic acid methyl ester 

Downstream Products

• 2999-46-4 Ethyl isocyanoacetate 
• 41995-26-0 benzyl isocyanoacetate 
• 39687-95-1 isocyanoacetic acid methyl ester 
• 2769-72-4 tert-Butyl isocyanoacetate 
• 109862-24-0 propyl isocyanoacetate 

Relevant academic research and scientific papers

Transition metal-free approach to azafluoranthene scaffolds by aldol condensation/[1+2+3] annulation tandem reaction of isocyanoacetates with 8-(alkynyl)-1-naphthaldehydes

A transition metal-free aldol condensation/[1+2+3] annulation reaction of isocyanoacetates with 8-(alkynyl)-1-naphthaldehydes has been developed for the general synthesis of azafluoranthenes. This domino reaction enables successive formation of three new bonds and two rings from readily accessible starting materials in a single operation. Furthermore, this methodology can also be utilized to construct chromeno[4,3-c]pyridines and benzo[c][2,6]naphthyridines in moderate yields.

Palladium-Catalyzed Divergent Imidoylative Cyclization of Multifunctionalized Isocyanides: Tunable Access to Oxazol-5(4 H)-ones and Cyclic Ketoimines

A palladium-catalyzed tunable imidoylative cyclization of multifunctionalized isocyanides to construct diverse imine-containing heterocycles has been developed. Oxazol-5(4H)-one derivatives were obtained exclusively when allyl-2-benzyl(or allyl)-2-isocyanoacetates were used in the reaction with aryl triflates as electrophiles, whereas cyclic ketoimines were generated in the presence of aryl iodides with the allyl ester group remaining unreacted. The reactions proceeded smoothly under mild conditions with a wide functional group tolerance.

A Peptide Backbone Stapling Strategy Enabled by the Multicomponent Incorporation of Amide N-Substituents

The multicomponent backbone N-modification of peptides on solid-phase is presented as a powerful and general method to enable peptide stapling at the backbone instead of the side chains. This work shows that a variety of functionalized N-substituents suitable for backbone stapling can be readily introduced by means of on-resin Ugi multicomponent reactions conducted during solid-phase peptide synthesis. Diverse macrocyclization chemistries were implemented with such backbone N-substituents, including the ring-closing metathesis, lactamization, and thiol alkylation. The backbone N-modification method was also applied to the synthesis of α-helical peptides by linking N-substituents to the peptide N-terminus, thus featuring hydrogen-bond surrogate structures. Overall, the strategy proves useful for peptide backbone macrocyclization approaches that show promise in peptide drug discovery.

One-pot synthesis of alternating peptides exploiting a new polymerization technique based on Ugi's 4CC reaction

We developed a one-pot synthetic technique for alternating peptides. Central to this technique is a new, catalyst-free polymerization based on Ugi's 4CC reaction. The treatment of imines with the ambident molecules bearing both an isocyanide and a carboxylic acid afforded alternating peptides.

Exploiting domino enyne metathesis mechanisms for skeletal diversity generation

In the context of diversity-oriented synthesis, the exploration and optimization of the domino metathesis of decorated norbornenes allowed complex polycyclic architectures to be generated in a highly efficient and atom-economical process. The Royal Society of Chemistry.

A rapid and simple cleanup procedure for metathesis reactions

Figure presented A new method for easy removal of ruthenium from metathesis reactions by using a polar isocyanide is reported. This protocol removed most ruthenium byproducts from a variety of synthetically useful metatheses. Moreover, the isocyanide-promoted carbene insertion results in rapid destruction of carbene reactivity, demonstrated in the commonly used first- and second-generation Grubbs' carbenes.

NOVEL PEPTIDES AS NS3-SERINE PROTEASE INHIBITORS OF HEPATITIS C VIRUS

The present invention discloses novel peptide compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such peptides as well as methods of using them to treat disorders associated with the HCV protease.

Novel peptides as NS3-serine protease inhibitors of hepatitis C virus

The present invention discloses novel compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.

Novel peptides as NS3-serine protease inhibitors of hepatitis C virus

The present invention discloses novel peptide compounds containing eleven amino acid residues which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compos

Novel peptides as NS3-serine protease inhibitors of hepatitis C virus

The present invention discloses novel peptide compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.