1051936-80-1

Basic information

• Product Name: (S)-5-(1-amino-2-phenylethyl)-N-phenyl-1,3,4-oxadiazole-2-amine
• Synonyms: (S)-5-(1-amino-2-phenylethyl)-N-phenyl-1,3,4-oxadiazole-2-amine
• CAS NO: 1051936-80-1
• Molecular Weight: 280.329
• Mol File: 1051936-80-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S)-5-(1-amino-2-phenylethyl)-N-phenyl-1,3,4-oxadiazole-2-amine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-5-(1-amino-2-phenylethyl)-N-phenyl-1,3,4-oxadiazole-2-amine(1051936-80-1)
• EPA Substance Registry System: (S)-5-(1-amino-2-phenylethyl)-N-phenyl-1,3,4-oxadiazole-2-amine(1051936-80-1)

Safety Data

• Hazardous Substances Data: 1051936-80-1(Hazardous Substances Data)

Upstream product

• 1051937-02-0 C₂₁H₂₄N₄O₃ 
• 1051936-71-0 tert-butyl (S)-(1-oxo-3-phenyl-1-(2-(phenylcarbamothioyl)hydrazinyl)propan-2-yl)carbamate 
• 103-72-0 phenyl isothiocyanate 
• 30189-48-1 (S)-tert-butyl (1-hydrazinyl-1-oxo-3-phenylpropan-2-yl)carbamate 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 63-91-2 L-phenylalanine 

Relevant articles and documents

Efficient synthesis of novel conjugated 1,3,4-oxadiazole-peptides

We were interested in the design and synthesis of novel bioisosteric analogues of leuprolide acetate containing the oxadiazole moiety at the C- or N-terminal of the peptide. An efficient approach for the synthesis of 2-amino-1,3,4-oxadiazoles through the reaction of hydrazide with ammonium thiocyanate and desulfurization reaction of the thiosemicarbazides using different coupling reagents was employed. These compounds are bioisosteres of the amide bond. Furthermore, the coupling of 2-amino-1,3,4-oxadiazoles at the C-terminal of leuprolide analogues was carried out, using a coupling reagent in the solution phase. On the other hand, the addition of a 2-amino-1,3,4-oxadiazole to the N-terminal of the peptide sequence was carried out through the reaction of the 2-amino-1,3,4-oxadiazole with succinic anhydride that led to the formation of a carboxylic acid moiety. Addition of the synthesized oxadiazole containing carboxylic acid to the peptide sequence was performed using a coupling reagent and on the surface of the resin. The synthesized peptides containing the oxadiazole moiety at the C- or N-terminal of the peptide sequence are peptidomimetics of leuprolide acetate. All of the synthesized peptides were purified using preparative HPLC and their structures were confirmed using HR-MS (ESI).

Parallel solution phase synthesis of a library of amino acid derived 2-arylamino-[1,3,4]-oxadiazoles

A mild method for the synthesis of peptidomimetic 2-arylamino 5-substituted 1,3,4-oxadiazoles from Boc-protected α-amino acid derived hydrazides has been developed, and applied in a parallel solution-phase synthesis. The optimized reaction conditions involve a one-pot reaction of Boc-protected amino acid hydrazides with arylisothiocyanates in the presence of either Hg(II) chloride, Mukaiyama's reagent (2-chloro-N-methylpyridinium iodide) or polymer supported Mukaiyama's reagent, with triethylamine in dichloromethane at ambient temperature. The 1,3,4-oxadiazole products were obtained in good to excellent yields without any detectable epimerization. The reactions proceed via initial formation of thiosemicarbazides, followed by dehydrothiolative cyclization to the 1,3,4-oxadiazoles.