Water → Ethyl 2-(2-aminothiazol-5-ylthio)acetate

Participants

Reaction Conditions

Reaction Steps

5-Bromo-2-aminothiazole (25 g, 96 mmol) and K2CO3 (26.5 g, 192 mmol) was suspended in DMF (50 mL) and stirred at 0° C. Ethyl thioglycolate (11.6 mL, 96 mmol) was added over 10 min. The reaction mixture was allowed to reach room temperature and stirred for a further 13 h. The mixture was divided between H2O (100 mL) and EtOAc (150 mL). Separation of the organic phase followed by extraction of the aqueous phase with EtOAc (2×100 mL). The combined organic phases were washed with aqueous NaHCO3 (2000 mL), brine (2×200 mL) and dried (MgSO4), filtered and evaporated. The crude product was dissolved in a small amount of DCM and purified by flash chromathography (SiO2, 2% TEA in EtOAc-heptane, from 30%->100%) to give 50-65% pure (2-aminothiazol-5-ylsulfanyl)acetic acid ethyl ester as a dark red-brown oil.

Provenance & Evidence