Large-scale oxidations in the pharmaceutical industry.

Unusual amino acids are fundamental building blocks of modern medicinal chemistry. The combination of readily functionalized amine and carboxyl groups attached to a chiral central core along with one or two potentially diverse side chains provides a unique three-dimensional structure with a high degree of functionality. This makes them invaluable as starting materials for syntheses of complex molecules, highly diverse elements for SAR campaigns, integral components of peptidomimetic drugs, and potential drugs on their own. This Perspective highlights the diversity of unnatural amino acid structures found in hit-to-lead and lead optimization campaigns and clinical stage and approved drugs, reflecting their increasingly important role in medicinal chemistry.

Unusual Amino Acids in Medicinal Chemistry.

Synthesis and reactivity of N-protected-α-amino aldehydes

The discovery of a series of non-peptide factor Xa (FXa) inhibitors incorporating 3-(S)-amino-2-pyrrolidinone as a central template is described. After identifying compound 4, improvements in in vitro potency involved modifications of the liphophilic group and optimizing the angle of presentation of the amidine group to the S1 pocket of FXa. These studies ultimately led to compound RPR120844, a potent inhibitor of FXa (K(i) = 7 nM) which shows selectivity for FXa over trypsin, thrombin, and several fibrinolytic serine proteinases. RPR120844 is an effective anticoagulant in both the rat model of FeCl(2)-induced carotid artery thrombosis and the rabbit model of jugular vein thrombus formation.

Design and structure-activity relationships of potent and selective inhibitors of blood coagulation factor Xa.

The stereochemistry of the osmium-catalyzed dihydroxylation of a series of chiral allylic amides and carbamates has been studied. The diastereoselectivity of these reactions was found to be dependent upon the solvent and the nitrogen protecting group as well as the geometry and substitution pattern of the olefin substrate. In contrast to the erythro selectivity observed with allylic alcohols, osmylations of the allylic amides and carbamates in this study were threo selective. Stoichiometric osmylations were consistently more selective than the corresponding catalytic reactions. Control experiments suggest this is due to the presence of a second catalytic cycle based upon an osmium glycolate catalyst which accumulates as the reaction proceeds to completion. Double diastereoselective dihydroxylations of allylic carbamates were also briefly examined.

Diastereoselectivity in the osmium-catalyzed dihydroxylation of allylic amides and carbamates

AN IMPROVED PREPARATION OF (S)-N-(BOC)-CYCLOHEXYLALANINAL. THE MOFFAT-SWERN OXIDATION OF α-AMINOALCOHOLS

An Efficient Process for the Synthesis of Renin Inhibitor, ABT-517

An Improved Preparation of (S)-N-(Boc)-Cyclohexylalaninal. The Moffat- Swern Oxidation of α-Amino Alcohols.

An efficient process for the preparation of renin inhibitor, ABT-517 is described. The process avoids solvent extractions or chromatographic purifications and is used on multi-kilogram scale.

An Efficient Process for the Synthesis of Renin Inhibitor, ABT-517.

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AN IMPROVED PREPARATION OF (S)-N-(BOC)-CYCLOHEXYLALANINAL. THE MOFFAT-SWERN OXIDATION OF α-AMINOALCOHOLS

An Efficient Process for the Synthesis of Renin Inhibitor, ABT-517

An Improved Preparation of (S)-N-(Boc)-Cyclohexylalaninal. The Moffat- Swern Oxidation of α-Amino Alcohols.

An Efficient Process for the Synthesis of Renin Inhibitor, ABT-517.