Ethyl 2-amino-3-sulfanylpropanoate → Ethyl 2-Amino-3-(2-furanylthio)propanoate

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Reaction Steps

To 16.25 g (125 mmol) of 2,5-dimethoxy-2,5-dihydrofuran and 23.20 g (125 mmol) of ethyl 2-amino-3-mercaptopropanoate in 100 ml dry acetonitrile was added approximately 0.15 g of tosyl chloride. The mixture was stirred 1 hour at room temperature under nitrogen during which time complete solution was attained which became very dark. The mixture was concentrated in vacuo, taken up in ethyl acetate, then extracted with aqueous NaHCO3 solution followed by saturated NaCl solution. The organic portion was dried over MgSO4, filtered then concentrated to 50 ml. The concentrate was then chromatographed to give 8.35 g (31.0%) of the title compound as a dark oil.

Provenance & Evidence