Dimethyl Sulfoxide → Ethyl 2-(4-(tert-butoxycarbonyl)piperazin-1-YL)thiazole-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

1,1-Dimethylethyl 1-piperazinecarboxylate (1.86 g, 10 mmol), methyl 2-chloro-5-thiazolecarboxylate (1.92 g, 10.0 mmol), diazabicycloundecene (1.5 mL, 10 mmol) and a catalytic amount of potassium iodide (2 mg) were dissolved in 10 mL of dry dimethylsulfoxide and warmed to 80° C. for 16 h. The warm solution was added dropwise with stirring to 200 mL of cold water. The reaction mixture was extracted with diethyl ether. The resulting extract was washed with water and brine, dried over magnesium sulfate and concentrated under reduced pressure to give 3.23 g of a yellow oil which solidified on standing. The solid was recrystallized from diethyl ether/hexanes to give 1.0 g of the title compound as light yellow crystals. This compound was of sufficient purity to use in subsequent reactions.

Provenance & Evidence