Triphenylphosphine → {1-[4-cyano-2-methyl-3-(trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl acetate

Participants

Reaction Steps

To a solution of 2-{[4-cyano-2-methyl-3-(trifluoromethyl)phenyl]amino}-2-oxoethyl acetate (Intermediate 46, 710 mg, 2.37 mmol) in tetrahydrofuran (20 mL) was added triphenylphosphine (1.24 g, 4.73 mmol), DIAD (0.920 mL, 4.73 mmol) and trimethylsilylazide (0.628 mL, 4.73 mmol). The reaction was stirred at room temperature for 18 hours. Solvent was removed under vacuum and residue was purified by silica chromatography (Biotage SP4, eluting 0% ethyl acetate in iso-hexane (2 column volumes), then a gradient from 0-50% ethyl acetate in iso-hexane (over 10 column volumes)). Pure fractions were combined and the solvent removed to yield the titled compound as a white solid (330 mg).

Provenance & Evidence