Hydrochloric Acid → HCID 90204562, compound

Participants

Reaction Steps

To a solution of 2-(tert-butylsulfinylamino)-N′-hydroxy-2-(3-methyloxetan-3-yl)acetamidine (example 254a, 0.25 g, 949 μmol) in isopropanol (5.00 ml) was added 1,1-dimethoxy-N,N-dimethylethanamine (506 mg, 3.8 mmol) and the reaction mixture was stirred at room temperature overnight. A solution of 4M hydrochloric acid in dioxane (1.19 ml, 4.75 mmol) was added to the reaction mixture cooled down to 0° C. and the reaction was stirred at 0° C. for 2 hours. The reaction mixture was diluted with ethyl acetate and extracted with a 2M aqueous solution of sodium carbonate. The organic phase was collected and the aqueous phase was back-extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a dichloromethane-methanol gradient to yield the title compound (35 mg, 20%) as a yellow oil which was not totally pure and was used without any further purification. MS (ESI, m/z): 184.1 (M+H+).

Provenance & Evidence