tert-Butanol → tert-butyl N-(1,3-thiazol-4-yl)carbamate

Participants

Reaction Steps

Thiazole-4-carboxylic acid (6.46 g, 50.0 mmol) was slurried in tert-butyl alcohol (280 mL). Triethylamine (7.68 mL, 55.1 mmol) and diphenylphosphonic azide (11.9 mL, 55.1 mmol) were added and the reaction mixture heated at reflux for 18 hours. The reaction mixture was concentrated in vacuo and the residue dissolved in ethyl acetate. The organics were washed successively with water, 5% aqueous citric acid solution, water, saturated aqueous sodium bicarbonate and brine. The organic phase was dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography (ISCO™ column, hexanes to ethyl acetate gradient elution) then triturated with 20% tert-butylmethyl ether in hexanes. The solid was collected by filtration and dried in vacuo to afford the title compound as a white solid (6.48 g).

Provenance & Evidence