138512-73-9

Upstream product

• 138423-75-3 (R)-2-(Allyl-tert-butoxycarbonyl-amino)-3-phenylselanyl-propionic acid methyl ester 
• 84348-39-0 (S)-1-tert-butyl 2-methyl 4-methylenepyrrolidine-1,2-dicarboxylate 
• 138423-70-8 (S)-N-allyl-N-(tert-butoxycarbonyl)-3-amino-2-oxetanone 
• 75-16-1 methylmagnesium bromide 
• 102195-80-2 (S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate 
• 5845-53-4 (R)-leucine methyl ester hydrochloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 123489-10-1 (R)-methyl 2-azido-4-methylpentanoate 
• 328-38-1 (R)-leucine 

Downstream Products

• 364750-81-2 N-tert-Butyloxycarbonyl-(2S,4S)-4-methylproline 
• 1250939-42-4 (2-(2-(4-bromophenyl)-2-oxoethyl)) 1-(tert-butyl) (2S,4S)-4-methylpyrrolidine-1,2-dicarboxylate 
• 1250939-45-7 C₁₉H₂₄BrN₃O₂ 
• 82111-44-2 leucinostatin A 
• 82111-44-2 leucinostatin A 

Relevant academic research and scientific papers

N-Heterocyclic Carbene Iron(III) Porphyrin-Catalyzed Intramolecular C(sp3)–H Amination of Alkyl Azides

Metal-catalyzed intramolecular C?H amination of alkyl azides constitutes an appealing approach to alicyclic amines; challenges remain in broadening substrate scope, enhancing regioselectivity, and applying the method to natural product synthesis. Herein we report an iron(III) porphyrin bearing axial N-heterocyclic carbene ligands which catalyzes the intramolecular C(sp3)–H amination of a wide variety of alkyl azides under microwave-assisted and thermal conditions, resulting in selective amination of tertiary, benzylic, allylic, secondary, and primary C?H bonds with up to 95 % yield. 14 out of 17 substrates were cyclized selectively at C4 to give pyrrolidines. The regioselectivity at C4 or C5 could be tuned by modifying the reactivity of the C5–H bond. Mechanistic studies revealed a concerted or a fast re-bound mechanism for the amination reaction. The reaction has been applied to the syntheses of tropane, nicotine, cis-octahydroindole, and leelamine derivatives.

HEPATITIS C VIRUS INHIBITORS

This disclosure concerns novel compounds of Formula (I) as defined in the specification and compositions comprising such novel compounds. These compounds are useful antiviral agents, especially in inhibiting the function of the NS5A protein encoded by Hepatitis C virus (HCV). Thus, the disclosure also concerns a method of treating HCV related diseases or conditions by use of these novel compounds or a composition comprising such novel compounds

Discovery and synthesis of HIV integrase inhibitors: Development of potent and orally bioavailable N-methyl pyrimidones

The human immunodeficiency virus type-1 (HIV-1) encodes three enzymes essential for viral replication: a reverse transcriptase, a protease, and an integrase. The latter is responsible for the integration of the viral genome into the human genome and, therefore, represents an attractive target for chemotherapeutic intervention against AIDS. A drug based on this mechanism has not yet been approved. Benzyl-dihydroxypyrimidine-carboxamides were discovered in our laboratories as a novel and metabolically stable class of agents that exhibits potent inhibition of the HIV integrase strand transfer step. Further efforts led to very potent compounds based on the structurally related N-Me pyrimidone scaffold. One of the more interesting compounds in this series is the 2-N-Me-morpholino derivative 27a, which shows a CIC95 of 65 nM in the cell in the presence of serum. The compound has favorable pharmacokinetic properties in three preclinical species and shows no liabilities in several counterscreening assays.

Preparation of 4-Alkylprolines by Intramolecular Radikal Cyclization of Chiral Serine Derivatives

N-Alkylation of the β-lactone derived from Boc-L-serine followed by ring opening with sodium benzeneselenoate provides chiral substrates which undergo intramolecular radical cyclization to afford cis/trans mixtures of 4-alkyl-L-prolines.