Ethanol → HCID 178468258, compound

Participants

Reaction Steps

3-Hydroxyisoxazole-5-carboxylic acid (23.3 mg, 181 μmol) and HATU (68.9 mg, 181 μmol) were combined in DMF (1 mL), and the resulting mixture was stirred for 5 minutes at room temperature. DIPEA (66 μL, 377 μmol) and (R)-3-[N-(4-bromo-benzyl)-hydrazino]-2-hydroxy-2-methyl-propionic acid ethyl ester (50 mg, 0.2 mmol) were added and the resulting mixture was stirred for 20 minutes. The mixture was the evaporated under reduced pressure, then combined with 5-chloro-2-fluorophenylboronic acid (47.4 mg, 272 μmol), K2CO3 (62.6 mg, 453 μmol), EtOH (0.7 mL, 10 mmol), and water (0.2 mL). SilicaCat®DPP-Pd (0.28 mmol/g loading; 53.9 mg, 15 μmol) was added and the resulting mixture was microwaved at 120° C. for 10 minutes. The mixture was filtered, and 1 M aqueous LiOH (604 μL, 604 μmol) was added. The mixture was stirred for 1 hour, then concentrated and purified by preparative HPLC to yield the title compound (33 mg, 94% purity). MS m/z [M+H]+ calc'd for C21H19ClFN3O6, 464.09; Found 464.1.

Provenance & Evidence