70817-57-1

Upstream product

• 96392-42-6 N-ethyl mandelamide 
• 201230-82-2 carbon monoxide 
• 109-89-7 diethylamine 
• 108-90-7 chlorobenzene 
• 1074-12-0 phenylglyoxal hydrate 
• 75-04-7 ethylamine 
• 611-73-4 Benzoylformic acid 
• 109-90-0 ethyl isocyanate 
• 98-86-2 acetophenone 
• 557-66-4 ethanamine hydrochloride 
• 627-45-2 N-formylethylamine 

Downstream Products

• 89843-13-0 (R)-N-ethyl mandelamide 
• 70817-58-2 (S)-α-hydroxy-N-ethyl-2-phenylacetamide 

Relevant academic research and scientific papers

Rapid assembly of α-ketoamides through a decarboxylative strategy of isocyanates with α-oxocarboxylic acids under mild conditions

A simple and practical method for α-ketoamide synthesis via a decarboxylative strategy of isocyanates with α-oxocarboxylic acids is described. The reaction proceeds at room temperature under mild conditions without an oxidant or an additive, showing good substrate scope and functional compatibility. Moreover, the applicability of this method was further demonstrated by the synthesis of various bioactive molecules and different application examples through a two-step one-pot operation.

Synthesis method of alpha-ketoamide compound

The invention discloses a synthesis method of an alpha-ketoamide compound. The preparation method comprises the following steps of: taking an isocyanate compound as shown in a formula I and a benzoylformic acid compound as shown in a formula II as raw mat

Electrochemical Synthesis of α-Ketoamides under Catalyst-, Oxidant-, and Electrolyte-Free Conditions

A catalyst-, oxidant-, electrolyte-free method for the preparation of α-ketoamides through the direct electrochemical amidation of α-ketoaldehydes and amines with innocuous hydrogen as the sole byproduct at ambient temperature was developed. The present reaction features clean and mild conditions, excellent functional-group tolerance, and high atom economy and scalability, enabling facile applications in pharmaceutical chemistry.

UV Assisted High-Efficient Synthesis of α-Ketoamides using Air Promoted by A Non-Metal Catalyst in Aqueous Solution

Presented here is the first example of UV (λ=210 nm) promoted procedure proceeding in aqueous media at room temperature using ambient air as the oxidant for efficient synthesis of an array of α-ketoamides of all types using a non-metal catalyst N-iodosuccinimide with a loading of 20 mol%. With UV, oxygen in the air was efficiently utilized as the green oxidant, some control experiments were carried out and a plausible mechanism was proposed, disclosing that in aqueous solution, the oxidation process was actually triggered by dioxygen radical anion (O2.?), while not molecular oxygen. A variety of secondary amines and primary amines as well as ammonia were employed as the amine moieties, and the desired product primary-, secondary-, and tertiary α-ketoamides were afforded in good to excellent yields of up to 96 %.

nBu4NI-Mediated oxidation of methyl ketones to α-ketoamides: using ammonium, primary and secondary amine-salt as an amine moiety

Presented here is the first example of synthesizing an array of primary-, secondary-, and tertiary-α-ketoamides with a non-metal catalyst nBu4NI from methyl ketones and inexpensive readily available amine/ammonium salts; the reactions proceeded smoothly under mild conditions, TBHP was used as an oxidant and the corresponding α-ketoamides were afforded in moderate to excellent yields.

Cu(ii)-catalyzed decarboxylative acylation of acyl C-H of formamides with α-oxocarboxylic acids leading to α-ketoamides

CuBr2-catalyzed decarboxylative acylation of the acyl C-H of N-monosubstituted and N,N-disubstituted formamides with α-oxocarboxylic acids leading to α-ketoamides was developed, which generated the corresponding products in good yields. The Royal Society of Chemistry 2013.

Direct use of formamides as amino group sources via C-N bond cleavage: A catalytic oxidative synthesis of α-ketoamides from acetophenones and formamides under metal-free conditions

An efficient and direct use of formamides as amino group sources for the synthesis of α-ketoamides was developed under metal-free conditions. The reaction was based on the oxidative coupling of acetophenones with formamides and generated the desired products in good yields in the presence of t-BuOOH/I2/PhCO2H.

Simplified procedure for TEMPO-catalyzed oxidation: Selective oxidation of alcohols, α-hydroxy esters, and amides using TEMPO and calcium hypochlorite

A wide range of primary and secondary multifunctional alcohols, α-hydroxyamides, and α-hydroxyesters were oxidized to their corresponding aldehydes, ketones, α-ketoamides, and α-ketoesters under mild reaction conditions using 2,2,6,6-tetramethylpiperidine-1-oxyl as a catalyst with calcium hypochlorite as an oxidant [TEMPO-Ca(OCl)2]. This simplified method does not require any transition metals, acids, or bases and demonstrates controlled and selective oxidation of structurally diverse alcohols, affording moderate to excellent yields at room temperature.

Biocatalytic reduction of α-keto amides to (R)-α-hydroxy amides using Candida parapsilosis ATCC 7330

Biocatalytic reduction of primary and secondary α-keto amides was accomplished using whole cells of Candida parapsilosis ATCC 7330. The primary (R)-α-hydroxy amides were obtained in good enantiomeric excess (up to 94%) and conversion (88-99%) as compared to the secondary (R)-α-hydroxy amides.

Carbonylation of aryl halides: Extending the scope of the reaction

Carbonylation reactions are being increasingly favoured in pharmaceutical chemistry for the atom-efficient introduction of carbonyl centres in aldehydes, acids, esters, and amides. Convenient procedures for simple aryl iodides and bromides are well established, and now the need is to develop improved conditions to allow the reactions to be extended to the more unreactive substrates, such as sterically hindered compounds and aryl chlorides. Sterically hindered compounds such as 2-iodo- or 2-bromo-m-xylenes can be converted using alkoxy and aminocarbonylation, while dehalogenation becomes a significant side reaction for reductive carbonylation. Less hindered compounds such as 2-iodo- or bromotoluene can be reacted successfully. Changing the aryl ligands of PdCl2{Ph2P(CH2)3PPh2} to alkyl groups improves the rate of oxidative addition but slows the carbonyl insertion step such that rates for the majority of aryl bromides are not improved by this change. Complexes such as PdCl2{Cy 2P(CH2)3PCy2} offer better performance for alkoxy and aminocarbonylation of aryl chlorides. However, for reductive carbonylation dehalogenation is a significant side reaction. Increasing CO pressure results in additional CO coordination to the catalytic intermediates and slows the reaction, while the dehalogenation is little affected, so reaction selectivity suffers. Thus, CO pressure is a critical parameter, particularly for reductive carbonylation, in achieving the optimum performance.