219738-95-1

Basic information

• Product Name: Aziridine, 1-[(4-nitrophenyl)sulfonyl]-2-(phenylmethyl)-, (2S)-
• CAS NO: 219738-95-1
• Molecular Formula: C15H14N2O4S
• Molecular Weight: 318.353
• Mol File: 219738-95-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Aziridine, 1-[(4-nitrophenyl)sulfonyl]-2-(phenylmethyl)-, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Aziridine, 1-[(4-nitrophenyl)sulfonyl]-2-(phenylmethyl)-, (2S)-(219738-95-1)
• EPA Substance Registry System: Aziridine, 1-[(4-nitrophenyl)sulfonyl]-2-(phenylmethyl)-, (2S)-(219738-95-1)

Safety Data

• Hazardous Substances Data: 219738-95-1(Hazardous Substances Data)

Upstream product

• 3182-95-4 L-Phenylalaninol 
• 63-91-2 L-phenylalanine 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 64501-87-7 2-(4-nitrophenylsulphonamido)-3-phenylpropanoic acid 

Downstream Products

• 1021495-62-4 {[(2S)-2-{[(4-nitrophenyl)sulfonyl]amino}-3-phenylpropyl]amino}acetic acid 
• 1021495-72-6 (2S)-3-phenyl-2-{[(2S)-2-{[(4-nitrophenyl)sulfonyl]amino}-3-phenylpropyl]amino}propanoic acid 
• 1021495-58-8 N-{(1S)-2-[(3-aminopropyl)amino]-1-benzylethyl}-4-nitrobenzenesulfonamide 
• 1021495-64-6 (2S)-N-(2-amino-2-oxoethyl)-1-[(2S)-2-{[(4-nitrophenyl)sulfonyl]amino}-3-phenylpropyl]pyrrolidine-2-carboxamide 
• 1021495-63-5 (2S)-1-[(2S)-2-{[(4-nitrophenyl)sulfonyl]amino}-3-phenylpropyl]pyrrolidine-2-carboxylic acid 
• 1021495-52-2 N-{(1S)-2-[(6-aminohexyl)amino]-1-benzylethyl}-4-nitrobenzenesulfonamide 
• 1021495-61-3 N-{(1S)-2-[4-(aminomethyl)piperidin-1-yl]-1-benzylethyl}-4-nitrobenzenesulfonamide 
• 312311-72-1 Ns-β³-hPhe-N-allyl-β³-hPhe-β³-hPhe-N-allyl-β³-hPhe-OMe 
• 312311-75-4 cyclo(N-(2-azidoethyl)-β³-hPhe-β³-hPhe-N-(2-azidoethyl)-β³-hPhe-β³-hPhe) 

Relevant articles and documents

Expedite protocol for construction of chiral regioselectively N-protected monosubstituted piperazine, 1,4-diazepane, and 1,4-diazocane building blocks

(Chemical Equation Presented) This paper describes the first study of solution-phase synthesis of chiral monosubstituted piperazine building blocks from nosylamide-activated aziridines. The protocol, involving aminolysis of the starting aziridines with ω-amino alcohols and subsequent Fukuyama-Mitsunobu cyclization, offers the advantage of mild conditions as well as short reaction times, and it leads to optically pure N-Boc- or N-Ns-protected piperazines. This four-step sequence, requiring only a single final chromatographic purification, was extended to include novel diazepane and diazocane derivatives.

β3-Amino acids by nucleophilic ring-opening of N-nosyl aziridines

N-Nosyl aziridines can be easily prepared from 1,2-amino alcohols derived from α-amino acids. Nucleophilic ring-opening of N-nosyl aziridines with cyanide ions followed by hydrolysis of the corresponding nitriles lead to N-nosyl β3-amino acids, which can be readily converted into a variety of derivatives bearing adequate functionality for peptide synthesis. The proposed methodology is simple, efficient, and amenable to large-scale preparations.

Deprotection of sulfonyl aziridines

The deprotection of the chiral N-sulfonyl aziridines 1-3 has been studied under different desulfonylation conditions. Two methods for the efficient aleprotection of 2-benzyl-, 2-phenyl-, and 2-carboxyl-N- sulfonylaziridines were found. The desulfonylation with lithium and a catalytic amount of di-tert-butyl biphenyl in THF at -78 °C led to the corresponding NH aziridines with yields up to 85%. Alternatively, the desulfonylation could be carried out with magnesium in methanol under ultrasonic conditions. The latter proved to be a very mild method and afforded the desulfonylated aziridines with yields up to 75%, even when the 2-phenyl substituted aziridine 2 was the studied substrate. Furthermore, in all the cases studied, no racemization was observed in the chiral center of the aziridines.