Phenol → (2S,4R)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-N-(4-(4-fluorophenoxy)phenyl)-4-phenoxypyrrolidine-2-carboxamide

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Reaction Conditions

Reaction Steps

Diisopropylazodicarboxylate (0.111 mL, 0.551 mmol) was added to a flask charged with (2S,4R)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-N-(4-(4-fluorophenoxy)phenyl)-4-hydroxypyrrolidine-2-carboxamide (233 mg, 0.551 mmol), prepared as in Reference 11, phenol (52 mg, 0.55 mmol), triphenylphosphine (145 mg, 0.551 mmol) and THF (3 mL). The reaction mixture was heated at 60° C. for 30 minutes and then concentrated. Product was purified from the residue by reverse phase HPLC to give Compound 259, (2S,4R)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-N-(4-(4-fluorophenoxy)phenyl)-4-phenoxypyrrolidine-2-carboxamide (15 mg, 0.012 mmol, 5% yield), as an off-white solid. 1H-NMR (400 MHz, DMSO-d6): 10.17 (s, 1H), 8.45 (s, 1H), 7.94 (s, 1H), 7.58 (d, J=8.8 Hz, 2H), 7.37-7.32 (m, 2H), 7.21-7.17 (m, 2H), 7.04-6.95 (m, 7H). MS (EI) for C27H24FN5O4. found 502.3 (MH+).

Provenance & Evidence