Chemical Properties
White to yellow or light brown crystal or powder
Uses
2-Amino-5-thiazolecarboxylic Acid Ethyl Ester is used in the synthesis of dual-action antidiabetic agents that inhibit glycogen phosphorylase.
Synthesis
1. N-bromosuccinimide (19.6 g, 0.11 mol) was slowly added to a water/dioxane (1:1, 100 mL) solution of ethyl 3-ethoxyacrylate (14.4 g, 0.1 mol) at -10 °C. 2. The reaction mixture was stirred at room temperature for 1 h. 3. After the addition of thiourea (7.6 g, 0.1 mol), the reaction mixture was was heated to 80 °C and maintained for 1 h. 4. Upon completion of the reaction, the solution was cooled to room temperature followed by the addition of ammonia (20 mL). 5. The resulting paste was stirred at room temperature for 10 min and then filtered. 6. The filter cake was washed with water and dried under vacuum to give the final product, ethyl 2-aminothiazole-5-carboxylate (12.1 g, 70% yield).
References
[1] Patent: EP2615092, 2013, A1. Location in patent: Paragraph 0095; 0096
[2] Patent: WO2006/8556, 2006, A1. Location in patent: Page/Page column 20-21