Triphenylphosphine → HCID 69707452, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-2-t-butoxycarbonylamino-3-[3-(2-cyanoethylaminocarbonyl)-benzyloxy]-propionitrile (3.8 g, 10.2 mmol) and triphenylphosphine (6.7 g, 25.5 mmol) in acetonitrile (75 mL) at 0° C. is added diisopropyl azodicarboxylate (5.0 mL, 25.5 mmol) and trimethylsilyl azide (3.73 mL, 28.1 mmol) dropwise, simultaneously, via syringe. The solution is then stirred at room temp. for 0.5 h, and then heated to 30° C. overnight. After solvent evaporation, the residue is taken up in EtOAc (150 mL), and then poured onto an ice—sat'd NaHCO3 mixture (150 mL), and extracted. The organic phase is washed with brine (100 mL), dried (MgSO4), evaporated and chromatographed (silica, 65% EtOAc/hexane) to yield (S)-2-t-butoxycarbonylamino-3-{3-[1-(2-cyanoethyl)-5-tetrazolyl]-benzyloxy}-propionitrile, as a light yellow oil.

Provenance & Evidence