Triethylamine → (1R)-1-Phenylethyl N-(5-(4-bromophenyl)-3-methyl-4-isoxazolyl)carbamate

Participants

Reaction Conditions

Reaction Steps

5-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carboxylic acid (2.0 g, 7.09 mmol) and triethylamine (0.99 mL, 7.09 mmol) were dissolved in toluene (50 mL). Diphenylphosphoryl azide (1.5 mL, 7.09 mmol) was added, followed by (R)-(+)-1-phenylethyl alcohol (0.865 g, 7.09 mmol; commercially available or prepared using procedures described herein or in the literature: e.g. E. J. Corey et al. J. Am. Chem. 1987, 109, 5551-5553), and the reaction was stirred at 80° C. for 4 hours. The mixture was concentrated, and the residue was purified by silica gel chromatography to give the title compound.

Provenance & Evidence