2-Methoxyethanol → HCID 86622893, compound

Participants

Reaction Conditions

Reaction Steps

Into a round bottom flask was placed 2-methoxyethanol (89.1 μL, 1.13 mmol), and triphenylphosphine (0.296 g, 1.13 mmol) under an atmosphere of nitrogen in THF (4.7 mL). The solution was cooled to 0° C. and diisopropyl azodicarboxylate (0.238 mL, 1.21 mmol) was added dropwise. After stirring for 15 min, N-(5-chloro-2-methylbenzyl)-3-[(trifluoroacetyl)amino]isoxazole-5-carboxamide (0.292 g, 0.807 mmol) in THF (4.7 mL) was added to reaction flask. The ice bath was removed and the resulting solution was stirred at rt for 15 h. The reaction solution was diluted with 1 N HCl and ethyl acetate. The aqueous layer was extracted with ethyl acetate once. The combined organic solutions were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography (30% ethyl acetate/hexs) to give the desired product as a white solid (300 mg, 89%). LCMS calculated for C17H18ClF3N3O4(M+H)+: m/z=420.1.

Provenance & Evidence