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 to 0° C. Ethyl thioglycolate (11.6 mL, 96 mmol) was added during 10 min. The reaction mixture was allowed to reach room temperature and stirred for further 16 h. Addition of water (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 chromatography (ISCO 330 g silica column, eluent A: heptane/B: 2% TEA in EtOAc. Gradient from 30% B->100% B.) to give 50-65% pure (2-aminothiazol-5-ylsulfanyl)acetic acid ethyl ester as a dark red-brown oil.

Provenance & Evidence