1-(Chloromethoxy)-2-methoxyethane → HCID 58822466, compound

Participants

Reaction Steps

(5R)-3-(3-Fluoro-4-{6-[(5S)-5-(hydroxymethyl)-4,5-dihydroisoxazol-3-yl]pyridin-3-yl}phenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (Example 1: 250 mg, 0.57 mmol), diisopropyl ethyl amine (238 μL, 1.37 mmol) and 2-methoxyethoxymethyl chloride (MEMCI) (78 μL, 0.68 mmol) were mixed in dry DMF (5 mL) and stirred at room temperature overnight. More diisopropyl ethylamine (250 μL, 1.44 mmol) and MEMCl (100 μL, 0.88 mmol) were added and it was stirred for another 6 hours. Again MEMCl (90 μL, 0.79 mmol) was added and it was stirred overnight. The solvent was evaporated under reduced pressure. Chromatography on silica gel with acetone/hexanes 3:1 and precipitation from dichloromethane/hexanes gave the product as off-white solid (261 mg).

Provenance & Evidence