83725-15-9

Upstream product

• 1189-71-5 isocyanate de chlorosulfonyle 
• 611-15-4 1-methyl-2-vinyl-benzene 
• 529-20-4 2-methylphenyl aldehyde 

Downstream Products

• 21464-57-3 ethyl 3-amino-3-(o-tolyl)propanoate 
• 752198-38-2 (R)-3-amino-3-(2-methylphenyl)propionic acid 
• 1448452-65-0 (S)-1-(hydroxymethyl)-4-(o-tolyl)azetidin-2-one 
• 1448452-67-2 (R)-1-(hydroxymethyl)-4-(o-tolyl)azetidin-2-one 
• 490034-62-3 (S)-3-amino-3-(o-tolyl)propanoic acid hydrochloride 
• 499794-59-1 (R)-3-amino-3-(o-tolyl)propanoic acid hydrochloride 
• 736131-48-9 (S)-3-amino-3-(2-methylphenyl)propionic acid 
• 1292457-13-6 ethyl (R)-3-amino-3-(o-tolyl)propanoate 
• 1293174-92-1 ethyl (S)-3-amino-3-(o-tolyl)propanoate 
• 1448452-64-9 1-(hydroxymethyl)-4-(o-tolyl)azetidin-2-one 

Relevant academic research and scientific papers

Easy access to constrained peptidomimetics and 2,2-disubstituted azetidines by the unexpected reactivity profile of α-lithiated N-Boc-azetidines

The reactivity profile of lithiated N-Boc-2-arylazetidines has been investigated filling a gap in the chemistry of this class of four-membered heterocycles. Two unexpected and unprecedented results have been observed: an "ortho-effect" accounting for the regioselective functionalization of the azetidine ring, and self-condensation leading to new and interesting azetidine-based peptidomimetics.

Enzymatic preparation of (S)-3-amino-3-(o-tolyl)propanoic acid, a key intermediate for the construction of Cathepsin inhibitors

Enantiomerically pure (S)-3-amino-3-(o-tolyl)propanoic acid [(S)-6], identified as the preferred enantiomeric form for the construction of novel β-amino acid derivatives as inhibitors of Cathepsin, was prepared through both indirect and direct enzymatic strategies. Resolution of hydroxymethylated β-lactam (±)-1 through Burkholderia cepacia lipase PSIM-catalysed R-selective butyrylation (E > 200) was first carried out in t-BuOMe. Treatment of the unreacted (S)-1 with 18% HCl then furnished the desired (S)-6·HCl. Next, Candida antarctica lipase B catalysed the ring cleavage of racemic 4-(o-tolyl)azetidin-2-one [(±)-2] with excellent R enantioselectivity (E > 200), either in t-BuOMe with added H2O as nucleophile or in H2O at 60 C. Hydrolysis of the less reactive β-lactam enantiomer [(S)-2] with 18% HCl afforded (S)-6·HCl. A direct enzymatic route to enantiomeric (S)-6 was finally optimized through the lipase PSIM-catalysed S-enantioselective (E > 200) hydrolysis of racemic ethyl 3-amino-3-(o-tolyl)propanoate [(±)-3] in t-BuOMe with added H 2O at 45 C or in H2O at 3 C.