219320-14-6

Upstream product

• 74786-02-0 1-(tert-butyldimethylsilyloxy)-1-tert-butoxyethylene 
• 99-90-1 para-bromoacetophenone 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 149104-90-5 4-acetylphenylboronic acid 
• 1694-31-1 tert-butyl acetoacetate 
• 13329-40-3 4-Iodoacetophenone 
• 540-88-5 acetic acid tert-butyl ester 

Downstream Products

• 950744-27-1 tert-butyl 2-[1-(1,4,7,10-tetraazacyclododecane)]-2-(4-acetylphenyl)acetate 
• 950744-24-8 (R/S)-tert-butyl 2-[1-(1,4,7,10-tetraazacyclodecane)-4,7,10-tris(tert-butylacetate)]-2-(4-acetylphenyl)acetate 

Relevant academic research and scientific papers

Synthesis of arylacetates by the palladium-catalyzed cross-coupling of aryl bromides and copper(II) enolates

Palladium-catalyzed cross coupling of aryl bromides and silylketene acetals in the presence of tributyltin fluoride or copper(II) fluoride is described.

3-PHOSPHOGLYCERATE DEHYDROGENASE INHIBITORS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

Copper-catalyzed coupling of aryl iodides and tert-butyl keto esters: Efficient access to α-aryl ketones and α-arylacetic acid tert-butyl esters

CuI/trans-4-hydroxy-l-proline catalyzed coupling of aryl iodides with tert-butyl keto esters proceeded smoothly at 40 °C in DMF, providing α-aryl ketones after acid-promoted deprotection and decarboxylation of tert-butyl ester group. While CuI/2-picolinic acid catalyzed coupling of aryl iodides with tert-butyl acetoacetate at 70 °C in dioxane delivered α-arylacetic acid tert-butyl esters upon spontaneous deacylation. A wide range of functional groups, such as acetyl, methoxy, nitrile, nitro, bromo, and chloro were compatible with the reaction conditions.

Palladium-catalyzed α-arylation of zinc enolates of esters: Reaction conditions and substrate scope

The intermolecular α-arylation of esters by palladium-catalyzed coupling of aryl bromides with zinc enolates of esters is reported. Reactions of three different types of zinc enolates have been developed. α-Arylation of esters occurs in high yields with i

CHELATING AGENT

A compound of the formula: wherein R1 is selected from H, methyl, ethyl, carboxyl protecting groups and hydrophilic moieties, R2 and R3 are independently selected from H, methyl, ethyl and carboxyl protecting groups, R4 is selected from H, methyl, ethyl, hydrophilic moieties and carboxyl protecting groups, and R5 is an aryl, heteroaryl, alkyl or a combination of these groups and is substituted with a carbonyl group, an aminooxy group or a functional group suitable for participating in a cycloaddition reaction. The compounds of the invention maybe useful as bifunctional chelating agents which allow chemoselective attachment to targeting molecules.

Synthesis of novel 1,4,7,10-tetraazacyclodecane-1,4,7,10-tetraacetic acid (DOTA) derivatives for chemoselective attachment to unprotected polyfunctionalized compounds

A convenient synthesis of novel bifunctional poly(amino carboxylate) chelating agents allowing chemoselective attachment to highly functionalized biomolecules is described. Based on the well known chelator 1,4,7,10- tetraazacyclodecane-l,4,7,10-tetraacetic acid (DOTA), we synthesized novel bifunctional chelating agents bearing additional functional groups by alkylating 1,4,7,10-tetraazacyclododecane (cyclen) with one equivalent of para-functionalized alkyl 2-bromophenyl-acetate and three equivalents of tert-butyl 2-bromoacetate. The resulting compounds, which contain an additional carbonyl or alkyne functionality, allow site specific labeling of appropriately functionalized unprotected biomolecules in a rapid manner via click reactions. This was demonstrated by the attachment of our new DOTA derivatives to the somatostatin analogue Tyr3-octreotate by chemoselective oxime ligation and CuI-catalyzed azide-alkyne cycloaddition. Initial biodistribution studies in mice with the radiometalated compound demonstrated the applicability of the described DOTA conjugation.