33684-12-7

Upstream product

• 108-30-5 succinic acid anhydride 
• 100-61-8 N-methylaniline 

Downstream Products

• 125735-87-7 1-diazo-5-(methylphenylamino)pentane-2,5-dione 
• 148902-18-5 methyl 4-(N-methyl-N-phenyl)amino-4-thiobutanoic acid 
• 148902-17-4 methyl 4-(N-methyl-N-phenyl)amino-4-thiobutanoate 
• 148902-22-1 ethyl 6-(N-methyl-N-phenyl)amino-3-oxo-6-thiooxhexanoate 
• 149825-77-4 ethyl 2-diazo-6-(N-methyl-N-phenyl)amino-3-oxo-6-thiooxhexanoate 
• 125735-95-7 6-(methylphenylamino)-2H-pyran-3(4H)-one 
• 7542-92-9 methyl β-(N-methyl-N-phenylamino)-acrylate 
• 4606-54-6 dimethyl 2-(methyl(phenyl)amino)maleate 
• 148902-16-3 methyl N-methyl-N-phenylsuccinimate 
• 110-15-6 succinic acid 
• 52190-10-0 N,N'-dimethyl-N,N'-diphenylsuccinamide 

Relevant academic research and scientific papers

A novel cycloaddition reaction of α-diazo-γ-amido ketones catalyzed by rhodium(II) acetate. Scope and mechanistic details of the process

α-Diazo ketones containing an amido group in the γ-position have been found to underdo a novel rhodium(II)-catalyzed cycloaddition reaction. Intramolecular cyclization of the keto carbenoid onto the oxygen atom of the amide group generates a carbonyl ylide dipole as a transient species. This highly stabilized dipole does not readily undergo 1,3-dipolar cycloaddition but ruther transfers a proton to produce a cyclic ketene N,O-acetal. The ketene acetale is unstable to moisture and upon standing is readily hydrolyzed to a γ-keto-δ-lactone and an amine. In the absence of any significant amount of water, the ketene N,O-acetal undergoes conjugate addition with the activated ?-bond of the dipolarophile to give a zwitterion intermediate. The anionic portion of the zwitterion adds to the neighboring carbonyl group. This is followed by epoxide ring formation with charge dissipation leading to an amido-substituted spiro cyclopentenyl epoxide. In certain cases a hydroxyl lactone was also isolated and its formation can be attributed to the competitive hydrolysis of the zwitterionic intermediate. The Rh(II)-catalyzed reaction of the diazo ketoamide derived from N-benzylpiperidone with DMAD afforded two different types of cyloadducts. In addition to the spiro cyclopentenyl epoxide, a product derived from trapping of the carbonyl ylide dipole was also obtained, thereby providing additional support for the proposed mechanism.

PEPTIDE DERIVATIVES

The invention concerns pharmaceutically useful trifluoromethyl ketone substituted di-, tri-and tetra-peptide derivatives of the formulae Ia, Ib, Ic set out hereinafter, and salts thereof, which are inhibitors of human leukocyte elastase. Also described herein are pharmaceutical compositions containing a peptide derivative and processes and intermediates for use in the manufacture of the peptide derivatives.