74963-37-4

Upstream product

• 5840-76-6 sarcosine-N-carboxyanhydride 
• 14856-79-2 N-benzyl(trimethylsilyl)amine 
• 100-46-9 benzylamine 
• 107-97-1 sarcosine 
• 2945-03-1 N-benzyl-2-bromoacetamide 
• 74-89-5 methylamine 
• 109-83-1 (2-hydroxyethyl)(methyl)amine 
• 124562-34-1 N-(tert-butyloxycarbonyl)sarcosine N'-benzylamide 

Downstream Products

• 108901-82-2 5-acetyl-3-methyl-4-thio-hydantoic acid benzylamide 
• 4801-77-8 N-benzyloxycarbonyl-N-methyl-glycine benzylamide 
• 64642-23-5 3-benzyl-2-difluoromethyl-1-methyl-2-oxo-2λ⁵-[1,3,2]diazaphospholidin-4-one 
• 64642-21-3 3-benzyl-1-methyl-2-oxo-2-phenyl-2λ⁵-[1,3,2]diazaphospholidin-4-one 
• 64642-22-4 3-benzyl-1-methyl-2-oxo-2-phenoxy-2λ⁵-[1,3,2]diazaphospholidin-4-one 
• 124562-35-2 N-Benzyl-2-[(2,2-diethoxy-ethyl)-methyl-amino]-acetamide 
• 124562-36-3 1-Benzyl-6-hydroxy-4-methyl-piperazin-2-one 
• 124562-37-4 1-Benzyl-4-methyl-6-oxo-piperazine-2-carbonitrile 
• 124562-39-6 1-Benzyl-4-methyl-6-oxo-1,4,5,6-tetrahydro-pyrazine-2-carbonitrile 
• 124562-38-5 4-Benzyl-1-methyl-5-oxo-piperazine-2-carbonitrile 
• 124581-10-8 (2R,3R,5S)-5-Benzylcarbamoyl-2-[3-((S)-1-ethoxycarbonyl-ethoxycarbonyl)-propionyl]-1-methyl-pyrrolidine-3-carboxylic acid (S)-1-ethoxycarbonyl-ethyl ester 
• 124562-42-1 (5R,6S)-3-Benzyl-4-[2-((R)-1-ethoxycarbonyl-ethoxycarbonyl)-eth-(E)-ylidene]-8-methyl-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-6-carboxylic acid (R)-1-ethoxycarbonyl-ethyl ester 
• 124562-42-1 (5R,6R)-3-Benzyl-4-[2-((R)-1-ethoxycarbonyl-ethoxycarbonyl)-eth-(E)-ylidene]-8-methyl-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-6-carboxylic acid (R)-1-ethoxycarbonyl-ethyl ester 

Relevant academic research and scientific papers

Protecting-Group-Free Amidation of Amino Acids using Lewis Acid Catalysts

Amidation of unprotected amino acids has been investigated using a variety of ‘classical“ coupling reagents, stoichiometric or catalytic group(IV) metal salts, and boron Lewis acids. The scope of the reaction was explored through the attempted synthesis of amides derived from twenty natural, and several unnatural, amino acids, as well as a wide selection of primary and secondary amines. The study also examines the synthesis of medicinally relevant compounds, and the scalability of this direct amidation approach. Finally, we provide insight into the chemoselectivity observed in these reactions.

Gold-Catalyzed Unexpected Ring Transformation of Pyrimidodiazepine Derivatives

Pyrimidodiazepine derivatives underwent an unexpected gold-catalyzed retro-Mannich-type carbon-carbon bond cleavage and intramolecular nucleophilic cyclization. The pyrimidodiazepines bearing an alkyne moiety showed novel orthogonal reactivity in the presence of a gold catalyst, as opposed to the alkynophilicity that is commonly observed with gold catalysts. The ring transformation reaction of pyrimidodiazepines probably proceeds through an acyclic iminium intermediate. The potential of this synthetic method for the skeletal diversification of pyrimidine-containing macrocycles was also demonstrated.

Ruthenium-catalysed oxidation of alcohols to amides using a hydrogen acceptor

A wider investigation into the synthesis of secondary amides from primary alcohols using a hydrogen acceptor using commercially available [Ru(p-cymene)Cl2]2 with bis(diphenylphosphino)butane (dppb) as the catalyst. The report looks at over 50 examples with varying functionality and steric bulk, whilst also covering the first reported results using microwave heating to effect the transformation.

Synthesis of amides from unprotected amino acids by a simultaneous protection-activation strategy using dichlorodialkyl silanes

Reaction of L-phenylalanine (1) with dichlorodimethylsilane or other dichlorosilane derivatives 6b-d and primary amines leads to the formation of amides probably via a cyclic silyl intermediate. It is also possible to use β-amino acids and N-alkylated amino acids (peptoid building blocks) as well as the amino dicarboxylic acid L-aspartic acid. The latter leads to almost exclusive formation of the α-amide.

Complex Pyrrolidines via a Tandem Michael Reaction/1,3-Dipolar Cycloaddition Sequence. A Novel Method for the Generation of Unsymmetrical Azomethine Ylides

A novel tandem Michael addition/1,3-dipolar cycloaddition protocol for the assembly of the 3,8-diazabicyclooctane ring system found in naphthyridinomycin (1) and quinocarcin (2) is described.