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

Participants

Reaction Steps

The product of Step 2 (9.00 g, 40.5 mmol) was taken up in 1,2-DCE (400 mL) before adding methyl 3-mercaptopropionate (9.74 g, 81 mmol) and zinc iodide (38.8 g, 122 mmol). The reaction was stirred at reflux for 5 h. The suspension was diluted with water and extracted with dichloromethane (2×). The combined organic layers were washed with brine, dried (Na2SO4), filtered and evaporated. Flash chromatography (0-15% ethyl acetate in hexanes) provided methyl 3-{[2-(5-bromo-1,3-thiazol-2-yl)propan-2-yl]sulfanyl}propanoate (12.58 g, 96%) as a colorless oil. ESI: [M+H]+ m/z 323.9/326.0.

Provenance & Evidence