Pyridine → HCID 59596669, compound

Participants

Reaction Steps

This compound was prepared in two batches under different conditions (Conditions A and B). In a closed vial 1,1-dimethylethyl (2S,5R)-2-(aminocarbonyl)-5-(4-hydroxyphenyl)-1-pyrrolidinecarboxylate (D13, 19 mg, 0.062 mmol), copper-(II)-acetate (11 mg, 0.062 mmol), (4-fluorophenyl)boronic acid (17 mg, 0.124 mmol) and molecular sieves were suspended in DCM. Then either pyridine (Condition A, 24.5 mg, 0.31 mmol) or triethylamine (Condition B, 31.3 mg, 0.31 mmol) was added and the reaction was shaken at room temperature for 24 h. The crude reaction products from Conditions A and B were combined, filtered and evaporated. The crude residue was purified by chromatography on silica gel using cyclohexanes/ethyl acetate (7:3) to afford the title compound (28 mg, 56%); Rt (HPLC): 5.61 min; MS: (ES/+) m/z: 423 [M+Na+], C22H25N2O4 requires 400; 1H NMR (400 MHz, DMSO-d6) δ ppm: 1.08 (s, 9H); 1.73-1.84 (m, 1H); 1.86-1.96 (m, 1H); 2.00-2.11 (m, 1H); 2.17-2.27 (m, 1H); 4.56-4.73 (m, 1H); 4.74-4.86 (m, 1H); 6.92 (br. s., 2H); 6.95 (br. s., 1H); 7.02 (br. s., 2H); 7.21 (t, 2H); 7.38 (s, 1H); 7.64 (br. s., 2H).

Provenance & Evidence