Pyridine → HCID 86760072, compound

Participants

Reaction Conditions

Reaction Steps

To an oven-dried, septaed 25 mL round-bottom flask, cooled under an argon atmosphere, and charged with (R)-N-BOC-valine (217.1 mg, 1.00 mmol) was added 2.5 mL CH2Cl2, and pyridine (81 μL, 1.00 mmol). The solution was cooled to −15 C, and to the reaction was added cyanuric fluoride (450 μL, 5.0 mmol). The reaction remained clear, but turned yellow green. The reaction was stirred at −15° C. for 60 minutes, with the gradual formation of a precipitate and transition to pale yellow. Without warming, the crude reaction was poured over ice and immediately extracted twice with CH2Cl2. The combined CH2Cl2 extracts were washed once with ice-cold water, dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford 222.2 mg of 25f as a white solid. FTIR (neat) 1844 cm−1.

Provenance & Evidence