88425-29-0

Upstream product

• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 543-27-1 isobutyl chloroformate 
• 57133-33-2 (S)-2-Azidocarbonyl-pyrrolidine-1-carboxylic acid benzyl ester 

Downstream Products

• 88425-30-3 N-(benzyloxycarbonyl)-2-(tert-butyloxy)pyrrolidine 
• 57133-32-1 2-(3-tert-butoxycarbonyl-ureido)-pyrrolidine-1-carboxylic acid benzyl ester 
• 57173-60-1 2-tert-butoxycarbonylamino-pyrrolidine-1-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Carbamoyl azides of α-N-protected amino acids: A fast and simple one-pot synthesis

A fast and simple one-pot synthesis of carbamoyl azides of α-N-protected amino acids is reported. The procedure involves the reaction between sodium azide and the mixed anhydride obtained from an α-N-protected amino acid and isobutyl chloroformate, in the presence of KH2PO4. The reaction rate was influenced by the nature of both the α-N-protection and the amino acid side chain. Surprisingly, tert-butyloxycarbonyl (α-N-Boc) and benzyloxycarbonyl (α-N-Cbz) protected proline afforded the corresponding isocyanates instead of the expected carbamoyl azides. Georg Thieme Verlag Stuttgart.

Amino Acids and Peptides. VI. Curtius Rearrangement of Acyl Amino Acid and Peptide Azides and Reactivity of the Isocyanates

Studies on the rate of Curtius rearrangement of acyl amino acid and peptide azides were carried out by means of IR (infrared) spectrophotometry at 25 deg.It was found that Z-Gly-N3 and Z-Pro-N3 were more stable than the other acyl amino acid azides.The re