Dimethyl Sulfide → HCID 86689165, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(di-tert-butoxycarbonyl-amino)-5-vinyl-pyrazine-2-carboxylic acid methyl ester (1 g, 2.64 mmol) and sodium bicarbonate (0.332 g, 3.95 mmol) in DCM (45 ml) and MeOH (15 ml) was cooled to −78° C. and purged with oxygen for 5 min. The reaction mixture was treated with ozone for 40 min until the mixture turned blue. The reaction mixture was purged with oxygen for 10 min and with nitrogen for 10 min, then dimethyl sulfide (0.487 ml, 6.59 mmol) was added at −78° C. and the mixture was allowed to warm to room temperature. The mixture was diluted with DCM and washed with 10% aq. sodium thiosulfate. The aq. layer was extracted with DCM and the combined organic layers were dried with Na2SO4 and evaporated to provide the title compound as yellow oil. The compound was used for the next step without further purification.

Provenance & Evidence