65037-88-9Relevant academic research and scientific papers
An improved synthesis of 5-acylamino-6-oxo-2-phenyl-1(6h)-pyrimidineacetic acid from glycine with readily removable protecting groups
Takahashi, Daisuke,Izawa, Kunisuke,Kashiwagi, Tatsumi,Onoye, Hiromi,Williams, Robert M.
, p. 2213 - 2229,17 (2020/08/31)
Concise synthesis of N-acyl-5-amino-6-oxo-2-phenyl-1(6H)- yrimidineacetic acid was achieved by cyclization reaction of 2-alkyl-4- lkoxymethylene-5(4H)- oxazolone with N-(carboxymethyl)benzamidine, while a similar reaction with sodium salt of 2-alkyl-4-hydroxymethylene-5(4H)- xazolones gave a mixture of regioisomers of the pyrimidinone. N-Acyl groups (acetyl or phenylacetyl) of the pyrimidinone derivatives were readily cleaved under very mild conditions with weak base or enzyme. Thus, the process enabled us to synthesize the drug candidate without exchanging N-protecting group. Since the starting oxazolones were easily prepared from N-acylglycine, the synthetic route can be used for the large scale synthesis of the key intermediate for several enzyme inhibitors.
Oxazolone copper(I) complexes inspired by the methanobactin active site
Jahnke, Ann Christin,Herter, Anastasia,Dechert, Sebastian,John, Michael,Meyer, Franc
scheme or table, p. 601 - 605 (2011/09/16)
Two oxazolone-derived potential ligands with enethioether substituents have been synthesized that differ by the terminal thioether moiety (S-Et in L 1, S-C6H4(OMe)-2 in L2). Both L 1 and L2 behave as bidentate {NS} chelate ligands to form stable complexes with copper(I) triflate that crystallize as dimeric complexes [L2Cu2(OTf)2] (4 and 5) featuring a central {Cu2S2} diamond core with distinctly different Cu-S bonds. L1 as well as 4 and 5 have been characterized by single crystal X-ray diffraction. NMR spectroscopy including 1H and 19F DOSY experiments reveals that 4 and 5 dissociate into monomeric species [LCu(OTf)] (4′ and 5′) in CDCl3 solutions. 4′ and 5′ retain the {NS} binding motif of the oxazolone-derived ligands, but are in slow equilibrium with their {OS} isomers 4″ and 5″ that result from E/Z isomerization of the exocyclic enethioether double bond.
Synthesis of (E)- and (Z)-Cyclopropyl-3-chloroalanine
Bland, John M.,Stammer, Charles H.,Varughese, Kottayil I.
, p. 1634 - 1636 (2007/10/02)
Both stereoisomers of cyclopropyl-3-chloroalanine (1) were synthesized by diazomethane cyclopropanation of the appropiate oxazolones (2).X-ray crystallographic analysis elucidated the configurations of 1 and gave some insight into its possible conformational preferences.
