Benzyl Alcohol → HCID 54488810, compound

Participants

Reaction Steps

To a suspension of 5.0 g (10.85 mmol) of 3,5-bis[(1-oxodecyl)amino]benzoic acid in 150 ml of anhydrous toluene cooled in an ice bath and stirred under an argon atmosphere was added 2.8 ml (13.0 mmol) of diphenylphosphoryl azide followed by 1.8 ml (13.0 mmol) of triethylamine. The reaction mixture was stirred in the ice bath for 1.5 hours, at room temperature for 1 hour and then at 90° C. for 2 hours. Benzyl alcohol (39 ml, 0.38 mol) was added and heating at 90° was continued for 4 hours. The solvent was removed at reduced pressure and most of the excess benzyl alcohol was removed at 80°/1 mm. NaHCO3 solution was added and the product was extracted with ethyl acetate. The dried extract was concentrated at reduced pressure and the residue was purified by HPLC using 25% ethyl acetate-hexane to give 27.8 g (45% yield) of [3,5-bis[(1-oxodecyl)amino]phenyl]carbamic acid phenylmethyl ester as a yellow foam. The nmr and mass spectra were compatible with the structure.

Provenance & Evidence