Uses
2-Amino-4-thiazoleglyoxylic Acid is an intermediate in synthesizing (6R,7R)-7-(2-(2-Aminothiazol-4-yl)-2-oxoacetamido)-8-oxo-3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid (A630310), which is used in the preparation of Cephalosporin C (C258750), an antibiotic used to study the effect of transpeptidase expression, binding, and inhibition on bacterial cell wall mucopeptide synthesis.
Synthesis
Under ice bath cooling conditions, 10.1 g of methyl 2-(2-aminothiazol-4-yl)thioacetoxy S-acid (CAS: 89721-50-6) was mixed with 80 mL of water, followed by the addition of 10.6 g of sodium carbonate. The reaction mixture was stirred continuously for 1 h at a maintained ice bath temperature. Upon completion of the reaction, the pH of the reaction mixture was adjusted to 2.5 at the same temperature using 6 N hydrochloric acid. the precipitated crystals were collected by filtration, washed with deionized water and subsequently dried to afford 6.2 g (67.8% yield) of 2-(2-aminothiazol-4-yl)glyoxalic acid with a melting point of more than 200°C. The infrared spectra of the product (KBr pressed slice) showed a νC=O absorption peak at 1660 cm?1.
References
[1] Patent: US4563534, 1986, A
