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Usage

Uses

Used in Pharmaceutical Synthesis:
Ethyl 2-oxo-2,3-dihydrooxazole-4-carboxylate is utilized as an intermediate in the synthesis of a variety of pharmaceuticals. Its unique structure and reactivity contribute to the development of new drugs, enhancing the therapeutic options available for various medical conditions.
Used in Agrochemical Production:
In the agrochemical industry, Ethyl 2-oxo-2,3-dihydrooxazole-4-carboxylate serves as a key intermediate for the production of various agrochemicals. Its incorporation aids in the creation of effective compounds designed to protect crops and enhance agricultural productivity.
Used as a Building Block in Organic Synthesis:
Beyond its applications in pharmaceuticals and agrochemicals, Ethyl 2-oxo-2,3-dihydrooxazole-4-carboxylate is also employed as a building block in organic synthesis. Its versatility allows for its use in the construction of complex organic molecules, facilitating advancements in the field of organic chemistry.

Upstream product

• 70-23-5 ethyl Bromopyruvate 
• 598-55-0 methyl carbamate 

Relevant academic research and scientific papers

Total synthesis and biological activity of neopeltolide and analogues

Combining the core structure of neopeltolide, lactone 16a, with the oxazole-containing side chain 23 via a Mitsunobu reaction provided the cytotoxic natural product neopeltolide (2). The side chain 23 was prepared from oxazolone 24 via the corresponding triflate. Key steps in the preparation of 23 were a Sonogashira coupling, an enamine alkylation, and a Still-Gennari Horner-Emmons reaction. By changing the Leighton reagent in the allylation step, the 11-epimer of lactone 16a, compound 50 was prepared. This led to 11-epi-neopeltolide 51. The 5-epimer of neopeltolide, compound 52, could be obtained from the minor isomer of the Prins cyclization. Furthermore, a range of analogues with modifications in the side chain were prepared. All derivatives were checked for toxicity effects on mammalian cell cultures and inhibitory effects on NADH oxidation in submitochondrial particles of bovine heart. Modifications in the lactone part are tolerated to some degree. On the other hand, shortening the distance between the oxazole and the lactone causes a significant drop in activity. Analogue 65 with an additional double bond is equally or even more active than neopeltolide itself.

Synthesis of 2-oxazolone-4-carboxylates from 3-nosyloxy- and 3-bromo-2-ketoesters

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.