1173817-68-9

Upstream product

• 95-14-7 1,2,3-Benzotriazole 
• 21027-01-0 N-benzyloxycarbonyl-L-alanyl-L-proline 
• 820239-42-7 benzyl N-[(1S)-2-(1H-1,2,3-benzotriazol-1-yl)-1-methyl-2-oxoethyl]carbamate 
• 1142-20-7 N-Cbz-Ala 

Downstream Products

• 27446-57-7 benzyl N-(1S)-2-[(2S)-2-(aminocarbonyl)tetrahydro-1H-pyrrol-1-yl]-1-methyl-2-oxoethylcarbamate 
• 1380332-76-2 cyclo(Z-L-Ala-D-Pro) 
• 36357-32-1 (3S,8aS)-3-methylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione 

Relevant academic research and scientific papers

A new benzotriazole-mediated stereoflexible gateway to hetero-2,5- diketopiperazines

Open chain Cbz-L-aa1-L-Pro-Bt (Bt=benzotriazole) sequences were converted into either the corresponding trans- or cis-fused 2,5- diketopiperazines (DKPs) depending on the reaction conditions. Thermodynamic tandem cyclization/epimerization afforded selectively the corresponding trans-DKPs (69-75%). Complementarily, tandem deprotection/cyclization led to the cis-DKPs (65-72%). A representative set of proline-containing cis- and trans-DKPs has been prepared. A mechanistic investigation, based on chiral HPLC, kinetics, and computational studies enabled a rationalization of the results. Stereoflexible route to DKPs: A convenient, versatile, and flexible benzotriazole-mediated methodology for the synthesis of proline-containing hetero-2,5-diketopiperazines (DKPs) is reported. Depending on the reaction conditions, either cis- or trans-configured DKPs were obtained starting from the same inexpensive l,l-dipeptidoyl benzotriazole key intermediate (see scheme). Kinetics, chiral HPLC, and computational studies forged a background for mechanistic rationalization. Copyright

Convenient synthesis of C-terminal di- and tri-peptide amides from N-protected dipeptidoylbenzotriazoles

N-Protected dipeptidoylbenzotriazoles react with aqueous ammonia to give dipeptide primary amides (77-98%) and with N-unprotected α-amino amides to afford tripeptide primary amides (82-86%).