Methyl 3-mercaptopropionate → Methyl 3-((5-bromothiazol-2-yl)methylthio)propanoate

Participants

Reaction Steps

5-Bromo-2-(bromomethyl)-1,3-thiazole (1.34 g, 5.22 mmol) was dissolved in DMF (15 mL). Methyl 3-mercaptopropionate (0.689 g, 5.74 mmol) and DIEA (0.876 g, 6.78 mmol) were added, and the reaction was stirred at room temperature for 3 h. The reaction was diluted with water and extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated. Flash chromatography (0-30% ethyl acetate in hexanes) afforded methyl 3-{[(5-bromo-1,3-thiazol-2-yl)methyl]sulfanyl}propanoate (1.45 g, 94%) as a pale yellow oil. MS BSI: [M+H]+ m/z 295.9/297.9.

Provenance & Evidence