Triethylamine → HCID 86707799, compound

Participants

Reaction Conditions

Reaction Steps

Diphenyl phosphoryl azide (93 μL, 0.43 mmol) is added to 3-fluoro-3-(4-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)cyclobutanecarboxylic acid (from Preparation 6 and Preparation 7, 200 mg, 0.39 mmol) along with triethylamine (66 μL, 0.47 mmol) and 2-trimethylsilylethanol (60 μL, 0.41 mmol) in THF (4.0 mL) and the mixture heated to 64° C. for 16 hours. After cooling to room temperature the mixture is partitioned between water (10 mL) and EtOAc (10 mL). The organics are separated, dried over MgSO4, filtered and evaporated to give a yellow oil, which is further purified using on regular silica from neat heptane to neat EtOAc to give the title compound (130 mg): 1H NMR (CDCl3) δ: 7.64-7.60 (4H, m), 7.46-7.44 (2H, m), 4.83 (1H, m), 4.14-4.09 (2H, m), 4.05 (2H, d), 3.64 (2H, d), 2.97-2.87 (2H, m), 2.66-2.56 (2H, m), 1.26-1.20- (1H, m), 0.96-0.91 (2H, m), 0.00 (9H, s).

Provenance & Evidence