75214-04-9

Upstream product

• 2985-39-9 2-benzylmalonic acid monoethyl ester 
• 2021-28-5 ethyl dihydrocinnamate 
• 101308-40-1 ethyl 2-bromo-3-phenylpropionate 

Downstream Products

• 1795-96-6 phenylalanine ethyl ester 
• 66299-29-4 (E)-N-Acetyl-α,β-didehydrophenylalanin-ethylester 
• 62436-67-3 ethyl (Z)-2-acetylamino-3-phenyl-2-propenoate 
• 223757-30-0 1,4-dibenzyl-5-hydroxy-2-tosylamino-4,5-dihydroimidazole 
• 223757-31-1 1,4-dibenzyl-2-tosylaminoimidazole 
• 223757-29-7 1,4-dibenzyl-4H-2-tosylaminoimidazol-5-one 
• 223757-45-7 N-(4-benzyl-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-4-methyl-benzenesulfonamide 
• 90237-81-3 N,N-Diacetyl-α,β-didehydrophenylalanin-ethylester 
• 51439-57-7 ethyl 2-acetamidocinnamate 
• 6613-41-8 ethyl 3-phenylpyruvate 

Relevant academic research and scientific papers

The synthesis of α-azidoesters and geminal triazides

Three simple methods for the synthesis of geminal triazides are described: Starting from 1) 3-oxocarboxylic acids, 2) iodomethyl ketones, or 3) terminal olefins, a range of triazidomethyl ketones can be constructed under mild oxidative reaction conditions by the use of IBX-SO3K, a sulfonylated derivative of 2-iodoxybenzoic acid (IBX), and NaN3 as an azide source. This is the first report of representatives of this novel class of triazide compounds: Despite their high nitrogen content, the geminal triazides are easy to handle, even when preparative-scale syntheses are performed. (Caution: These procedures still require protective measures!) The triazides are now broadly available for further studies regarding their properties and reactivity. Furthermore, we show how the method can be used to provide α-azidoesters, which are potential building blocks for amino acids. Either/or: Geminal triazides are rapidly constructed with broad scope by the use of oxocarboxylic acids, iodomethyl ketones, or terminal olefins as starting substrates in oxidative azidations with a mild derivative of 2-iodoxybenzoic acid and sodium azide. Along with this little-studied class of organic azides, α-azidoesters were also synthesized.

Synthesis ofα-azido ketones and esters using recyclable hypervalent iodine reagent

A simple and mild method for the preparation of αazido ketones and esters using hypervalent iodine reagent, 4,4'-bis-(dichloroiodo)-biphenyl, and sodium azide in 1,4-dioxane is discussed. Advantages of this system are easy workup, recyclable reagent, and

Amino Acids, 2. N-Acetyl α,β-Didehydro α-Amino Acid Esters from α-Azidocarboxylic Acid Esters and Acetic Anhydride by Nitrogen Elimination with Rhenium Catalysts

α-Azidocarboxylic acid esters 2 react with acetic anhydride in presence of catalytic amounts of rhenium heptasulfide and - if necessary - by addition of hydrochloric acid to give N-acetyl 3 or/and N,N-diacetyl-α,β-didehydro-α-amino acid esters 4 in very g

Reaction of α-Azido Esters with Lithium Ethoxide: Synthesis of Dehydroamino Esters and α-Keto Esters

α-Azido esters 4 react with catalytic amounts of ethoxide in tetrahydrofuran/ethanol to evolve nitrogen and form dehydroamino esters 3.Acid hydrolysis gives α-keto esters 5 in good yields.