5501-26-8

Upstream product

• 100-51-6 benzyl alcohol 
• 24469-50-9 t-butyl 3-benzylidenecarbazate 
• 53370-84-6 N'-benzylhydrazinecarboxylic acid tert-butyl ester 
• 100-52-7 benzaldehyde 
• 287728-91-0 N-benzyloxycarbonylaminophthalimide 
• 5331-43-1 N-benzyloxycarbonyl-hydrazine 
• 501-53-1 benzyl chloroformate 
• 555-96-4 Benzylhydrazine 
• 287729-07-1 N-benzyl-N-benzyloxycarbonylaminophthalimide 
• 57699-97-5 N^α-benzyl-N^α-(benzyloxycarbonyl)-N^β-(tert-butyloxycarbonyl)hydrazine 

Downstream Products

• 485831-49-0 N-benzyl-N'-(2-tert-butoxycarbonylamino-3-hydroxy-propionyl)-hydrazinecarboxylic acid benzyl ester 

Relevant academic research and scientific papers

Capture-ROMP-release: Application to the synthesis of amines and alkyl hydrazines

Application of a capture-ROMP-release strategy for the chromatography-free purification of Mitsunobu reaction products is described. Norbornenyl-tagged reagents are utilized for standard solution phase Mitsunobu chemistry. Post-reaction phase-switching is accomplished via in situ ring-opening metathesis polymerization (ROMP) followed by precipitation of the polymer with methanol. Release of the product from the polymer affords amines and alkyl hydrazine derivatives with good yields and purities.

The synthesis of azapeptidomimetic beta-lactam molecules as potential protease inhibitors.

Synthetic methods for the construction of a novel peptidomimetic structure are reported. The structure incorporates a beta-lactam and an azapeptide in a peptide backbone with the intention of generating rationally designed substrate-based protease inhibitors. The beta-lactam is formed by subjecting serine or threonine-azapeptides to Mitsunobu reaction conditions. Importantly, the azapeptidomimetic beta-lactam structure permits extended binding inhibition and the synthetic methods to create tetrapeptidomimetic structures are described.

New Synthesis of 1,1-Substituted Hydrazines by Alkylation of N-Acyl- or N-alkyloxycarbonylaminophthalimide Using the Mitsunobu Protocol

N-acyl- and N-alkoxycarbonylaminophthalimides are prepared using a convenient reaction and are efficiently used as acid partners in Mitsunobu reaction. This reaction allows them to be alkylated by primary, secondary or benzyl groups. Comparison of the reactivities and pKa values of these N-substituted aminophthalimides suggest that the success of the Mitsunobu reaction in this case seems to be governed more by steric than by electronic effects. A final dephthaloylation step results in an efficient method for the preparation of 1,1-substituted hydrazines.