Sodium hydride → 2-tert-Butoxycarbonylamino-3-(4-fluoro-phenylsulfanyl)-propionic Acid Methyl Ester

Participants

Reaction Steps

A stirred solution of 4-fluorothiophenol (1.24 g, 9.65 mmol) in N,N-dimethyl formamide (10 ml) was treated with sodium hydride (240 mg, 9.37 mmol) and the reaction mixture was stirred at room temperature for 30 minutes. 2-tert-Butoxycarbonylamino-3-(toluene-4-sulfonyloxy)-propionic acid methyl ester (3 g, 8.04 mmol) in N,N dimethyl formamide (ml) was added, the resulting mixture was stirred for two hours and then concentrated in vacuo. The residue was dissolved in ethyl acetate (100 ml) and washed with water (2*80 ml) and brine. The organic layer was dried (anhydrous magnesium sulfate) and concentrated in vacuo to give, after purification by flash chromatography on silica gel, 2-tert-butoxycarbonylamino-3-(4-fluoro-phenylsulfanyl)-propionic acid methyl ester (2.28 g, 83%) as a yellow oil.

Provenance & Evidence