Pyridine → HCID 58758416, compound

Participants

Reaction Steps

(5R)-3-(3-Fluoro-4-{6-[(5S)-5-(hydroxymethyl)-4,5-dihydro-3-isoxazolyl]-3-pyridinyl}phenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (Example 1, 60 mg, 0.13 mmol) was suspended in 2 mL of anhydrous dimethylformamide. Anhydrous pyridine (1 mL, 12 mmol), 4-dimethylaminopyridine (DMAP) (10 mg, 0.08 mmol) and glutaric anhydride (75 mg, 0.55 mmol) were added and the solution was stirred for 16 hours at room temperature during which the mixture became a clear solution. The reaction was quenched with 1 mL of methanol and purged with diazomethane generated from 1-methyl-3-nitro-1-nitrosoguanidine (MNNG) in a diazomethane generator (Aldrich, cat. No. Z41,173–6) until all product was converted into its methylester as judged by LCMS and the solution turned yellow. The solvent was removed and the product purified by chromatography on silica using a gradient from 0–10% methanol in dichloromethane that yielded 31 mg (40%) of the title compound as a white solid.

Provenance & Evidence