3969-02-6Relevant articles and documents
Oxidation of didehydro-α-amino acids as a route to β-hydroxy-or β-amino-pyruvic derivatives and to α-acylglycinates
Miossec, Benoit,Rudyk, Helene,Toupet, Loic,Danion-Bougot, Renee,Danion, Daniel
, p. 1833 - 1837 (1996)
Oxidation of protected didehydro-α-amino acids with N-bromosuccinimide or lead tetraacetate affords imines of β-bromo- or β-acetoxy-pyruvates. The hydrolysis of brominated imines proceeds through addition of water followed by intramolecular displacement o
COMPOUNDS TO TREAT AMYLOIDOSIS AND PREVENT DEATH OF BETA-CELLS IN TYPE 2 DIABETES MELLITUS
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Page/Page column 52, (2010/11/24)
The invention discloses aromatic amides and sulfonates to treat or prevent type 2 diabetes mellitus (T2DM), the pathological consequences of T2DM, to inhibit amyloidosis or to prevent death of β-cells of the pancreas.
Synthesis of 2-oxazolone-4-carboxylates from 3-nosyloxy- and 3-bromo-2-ketoesters
Okonya, John F.,Hoffman, Robert V.,Johnson, M. Catherine
, p. 1102 - 1108 (2007/10/03)
New methods for the synthesis of 2-oxazolone-4-carboxylates from 3-nosyloxy- and 3-bromo-2-ketoesters are described. Condensation of 3-nosyloxy-2-ketoesters with methyl carbamate in refluxing toluene in the presence of p-TSA provided 2-oxazolone-4-carboxylates in good yields (41-80%). Alternatively, bromination of α-ketoesters with CuBr2 provided 3-bromo-2-ketoesters which condensed with methyl carbamate in the presence of p-TSA and AgOTfunder similar conditions to provide 2-oxazolone-4-carboxylates in comparable yields (30-79%). The 2-oxazolone-4-carboxylates bear functionality that can be elaborated to a variety of potentially useful compounds. For example, some of these heterocycles were readily N-acylated, reduced to alcohols, or saponified and coupled with amino acids.
Synthesis of 4-carboethoxy-4-oxazolin-2-ones from 3-nosyloxy-2-ketoesters
Hoffman, Robert V.,Johnson, M. Catherine,Okonya, John F.
, p. 1283 - 1286 (2007/10/03)
3-Nosyloxy-2-ketoesters, available from 2-ketoesters, react efficiently with methyl carbamate and tosic acid in refluxing toluene to provide 4-carboalkoxy-4-oxazolin-2-ones in good yields (41-84%).