Acid-facilitated debenzylation of N-Boc, N-benzyl double protected 2-aminopyridinomethyl pyrrolidine derivatives

Abstract

2-Aminopyridinomethyl pyrrolidines represent a class of highly potent and selective neuronal nitric oxide synthase inhibitors. Conditions for a Mitsunobu reaction of a naphthol and a hindered secondary alcohol were optimized to give good to excellent yields. A key step in the synthesis of these inhibitors is the deprotection of the benzyl group from the N-Boc and N-Bn double protected 2-aminopyridine ring at a late stage of the synthesis, which has been proven difficult in our previous syntheses. Acetic acid was found to facilitate the N-Bn deprotection.

Novel Route for Synthesis of Anti - Hyperglycaemic Activity of Thiazolidine 2,4- Dione Derivatives As A Mannich Bases

“…The crude compounds were purified using column chromatography (100-200 mesh silica) and Combi-flash chromatography. The hydrogenolysis process was carried out using parr shaker [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19].…”

Phosphine‐Activated Lysine Analogues for Fast Chemical Control of Protein Subcellular Localization and Protein SUMOylation

“…The UAA mutagenesis approach requires minimal engineering of the protein of interest; when the proper orthogonal translational machinery is provided, UAAs are incorporated simply by mutating the codon at the desired position to the amber stop codon . UAAs allow investigators to site‐specifically insert new chemical functionalities into proteins, thereby enabling small‐molecule control in live biological systems . For example, palladium complexes can trigger protein function using propargylated or allylated lysine and allenylated tyrosine .…”

Highly Efficient Lipase Catalyzed Monoaminolysis Reaction of Diesters with Benzylamine

“…Synthesis of monoamides(5) and(6) by desymmetrization lipase catalyzed aminolysis of diesters diethyl malonate (1) and diethyl succinate (2) with amine (4) in an organic solvent.…”

“…The benzyl group is commonly used as a protecting group in different synthetic procedures and is typically cleaved using reductive methods to obtain amino or amide groups, as in ethyl 3-amino-3-oxopropanoate (7). 5 Initially, the enzymatic aminolysis of diethyl malonate (1) with amine (4) was tested. All reactions were conducted at several temperatures (30°C-60°C), in an organic solvent, using near equimolecular amounts of reagents, and the reactions were stopped when no further progress was observed by thin layer chromatography (TLC).…”

“…The benzyl group is commonly used as a protecting group in different synthetic procedures and is typically cleaved using reductive methods to obtain amino or amide groups, as in ethyl 3-amino-3-oxopropanoate ( 7 ). 5…”