Methanesulfonyl chloride → HCID 86651336, compound

Participants

Reaction Steps

To a solution of benzyl (RS)-2-((RS)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-hydroxypropylcarbamate (0.843 g, 2.73 mmol) in dry dichloromethane (30 mL) was added diisopropylethylamine (1.351 ml, 8.18 mmol) and then methanesulfonyl chloride (0.274 ml, 3.54 mmol) and the resulting solution was stirred at RT. After 15 mins it was washed with water, dil HCl, and sat aq NaHCO3 and then processed normally. A solution of the crude product in DMF (15 mL) was treated with sodium thiomethoxide (0.573 g, 8.18 mmol) and the mixture was stirred at RT for 1 h. Then toluene was added and the mixture was washed with water (×2) and processed normally. Chromatography (EtOAc/Hex 1:2) gave benzyl (SR)-2-((RS)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-(methylthio)propylcarbamate (0.77 g, 2.268 mmol, 83% yield) as a syrup. 13C NMR (CDCl3) δ156.9, 136.9, 128.9, 128.5, 128.5, 109.3, 76.8, 67.7, 67.1, 41.9, 33.7, 26.9, 25.6, 16.6.

Provenance & Evidence