Triethylamine → [5-(4-Bromophenyl)-3-methylisoxazol-4-yl]carbamic acid 1-(2-chlorophenyl)ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a suspension of 5-(4-bromo-phenyl)-3-methyl-isoxazole-4-carboxylic acid (7.0 g, 24.8 mmol) and triethylamine (3.46 g, 24.8 mmol) in toluene (250 mL) was added diphenylphosphoryl azide (5.31 mL, 24.8 mmol), followed by 2-chloro-alpha-methylbenzyl alcohol (3.88 g, 24.8 mmol), and the reaction was stirred at 80° C. for 2.5 hours. The mixture was partitioned between EtOAc and H2O, and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was dissolved in EtOAc and filtered through Celite to remove a precipitate that was present. The crude material was purified by silica gel chromatography to give the title compound.

Provenance & Evidence