The stereoselective synthesis of cathepsin inhibitors from indoline type epoxyamides is described. The use of this type of epoxyamides permitted the preparation of E-64 and CA-074 related compounds depending on the order in which the key steps, the oxidation of indoline amides to indole amides and oxidative acetal cleavage were undertaken. By taking advantage of the facile substitution of the i...

The synthesis of α-amino carbonyl/carboxyl compounds is a contemporary challenge in organic synthesis. Herein, we present a stereoselective α-amination of amides employing simple azides that proceeds under mild conditions with release of nitrogen gas. The amide is used as the limiting reagent, and through simple variation of the azide pattern, various differently substituted aminated products c...

Heretofore the amides of glucuronic, galacturonic, and mannuronic acid were not known, and methods were not available for their preparation. It has now been found possible to obtain the amides of uronic acids from the corresponding 1-amino-uronamides by selective hydrolysis of the glycosylamino group. An aqueous solution of the 1-amino-uronamide is treated with an acid or a suitable cation exch...

The mixed anhydrides with N-acyl carbamic acid (IV) were prepared by the reaction of carboxylic acids (Ill) with N-chlorocarbonyl lactams (Ila) or sec. amides (lib). Decarboxylation of IV yielded N-acyl lactams (VI), while symmetrical anhydrides (VII) were obtained by the side reaction of IV with carboxylic acids (III). Aminolysis of IV yielded carboxylic acid amides (IX) in high yield and puri...

2-Ns-Protected β-amino Weinreb amides were synthesized by aminochlorination of α,β-unsaturated Weinreb amides in an ionic liquid, 1-n-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide ([BMIM][NTf2]). Processed without the use of metal catalysts or the need of an inert gas atmosphere, the presented process can be readily performed as a one-pot synthesis at room temperature. Moreover, ...

The reaction of glycine-N-methyl amide with paraformaldehyde in the presence of ytterbium triflate (1 mol%) leads to a novel cage structure 6 which is chiral at nitrogen. Single crystal X-ray analysis and DFT calculations suggest this cage structure is rigid and adopts a single low energy conformation. Use of single enantiomer α-amino amides results in two diastereomeric tertiary amines that di...