Pyridine → HCID 58758457, 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 (MAP) (10 mg, 0.08 mmol) and cis-hexahydrophthalic anhydride (85 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 diazomethanegenerator (Aldrich, cat. No. Z41,173-6) until all product was converted into its methyl ester as judged by LCMS and the solution turned yellow by excess diazomethane. The solvent was removed and the product purified by chromatography on silica using a gradient from 0–20% methanol in dichloromethane that yielded 40 mg (48%) of the title compound as an off white solid.

Provenance & Evidence