4561-35-7

Upstream product

• 2901-75-9 (R,S)-N-acetyl phenylalanine 

Downstream Products

• 55152-22-2 3-benzyl-5-methyl-1,2,4-oxadiazole 
• 4561-36-8 N-acetyl-1-amino-1-methoxy-2-phenylethane 
• 1722-84-5 (E)-N-styrylacetamide 
• 122-78-1 phenylacetaldehyde 
• 140-29-4 phenylacetonitrile 
• 25692-18-6 methyl 2-methoxy-3-phenylpropanoate 
• 78814-96-7 (RS)-2-methoxy-3-phenylpropanoic acid 
• 828-01-3 phenyllactic acid 
• 64-19-7 acetic acid 
• 103979-36-8 C₁₂H₂₃N*C₁₁H₁₂N₂O₄ 
• 24748-46-7 α-benzyl-α-(acetylamino)acetonitrile 

Relevant academic research and scientific papers

Rearrangement of Carboxylates derived from N-Acetyl-N-nitroso-&α-amino-acids

While N-acetyl-N-nitrosophenylalanine thermally decomposes by the known mechanism, its carboxylate anion undergoes facile rearrangements initiated by carboxylate attack in methanol or water to give 2-methoxy- or 2-hydroxy-3-phenylpropanoic acid, respectively.

N-acyl-N-nitrosoamino acids and peptides

N-acylamino acids and peptides are readily nitrosated by N2O4 and the products can be readily isolated. Hydrolysis of the N-nitrosoacylamino acids and polynitrosoacylpeptides in aqueous media (pH 1-8) occurs preferentially from the C-terminus.

THE PHOTOELIMINATION OF N-NITROSO-N-ACETYL-α-AMINO-ACIDS; A NEW SYNTHESIS OF 1,2,4-OXADIAZOLES

The excitation of N-nitroso-N-acetyl-α-aminoacids, nitrosopeptide model compounds, under neutral and weakly basic conditions, caused the homolysis of the N-N bond followed by decarboxylation to give hyponitrous acid (HNO) and N-acetylimines which were susceptible to nucleophilic addition.While weak bases caused the carboxylate group to assist intramolecular rearrangement to a small extent, they functioned primarily to provide nucleophilic NO-, which initiated nucleophilic attack leading to the C-nitroso derivatives.These C-nitroso derivatives spontaneously cyclized to 1,2,4-oxadiazoles much more rapidly than tautomerism to the corresponding oximes; the latter oximes failed to cyclize under the basic conditions.