Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, ACS Catalysis called Zn-Catalyzed tert-Butyl Nicotinate-Directed Amide Cleavage as a Biomimic of Metallo-Exopeptidase Activity, Author is Wybon, Clarence C. D.; Mensch, Carl; Hollanders, Charlie; Gadais, Charlene; Herrebout, Wouter A.; Ballet, Steven; Maes, Bert U. W., which mentions a compound: 1445085-77-7, SMILESS is O=S(O[Pd]C1=CC=CC=C1C2=C(C=CC=C2)N)(C)=O.CC(C)OC3=CC=CC(OC(C)C)=C3C4=CC=CC=C4P(C5CCCCC5)C6CCCCC6, Molecular C43H56NO5PPdS, SDS of cas: 1445085-77-7.
A two-step catalytic amide-to-ester transformation of primary amides under mild reaction conditions has been developed. A tert-Bu nicotinate ( tBu nic) directing group is easily introduced onto primary amides via Pd-catalyzed amidation with tert-Bu 2-chloronicotinate. A weak base (Cs2CO3 or K2CO3) at 40-50°C can be used provided 1,1′-bis(dicyclohexylphosphino)ferrocene is selected as ligand. The tBu nic activated amides subsequently allow Zn(OAc)2 catalyzed non-solvolytic alcoholysis in tBuOAc at 40-60°C under neutral reaction conditions. The activation mechanism is biomimetic: the C3-ester substituent of the pyridine in the directing group populates the trans-conformer suitable for Zn-chelation, C=O(amide)-Zn-N(directing group) and Zn-coordinated alc. is addnl. activated as a nucleophile by hydrogen bonding with the acetate ligand of the catalyst. Addnl., the acetate ligand assists in intramol. O-to-N proton transfer. The chemoselectivity vs. other functional groups and compatibility with challenging reaction partners, such as peptides, sugars and sterols, illustrates the synthetic applicability of this two-step amide cleavage method. The tBu nic amides do not require purification before cleavage. Preliminary experiments also indicate that other weak nucleophiles can be used such as (hetero)arylamines (transamidation) as exemplified by 8-aminoquinoline.
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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem