Tetrahydrofuran → HCID 90204489, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(5-Methyl-[1,2,4]oxadiazol-3-yl)-propionic acid ethyl ester (CAN168704-76-5, 0.5 g, 2.71 mmol) in a mixture of dry THF (15 ml)/dry DMF (4 ml) cooled down to 0° C. under an argon atmosphere was slowly added LiHMDS 1.0M solution in THF (2.85 ml, 2.85 mmol). The reaction mixture was stirred at 0° C. for 30 minutes followed by addition of O-(diphenylphosphoryl)hydroxylamine (696 mg, 2.99 mmol). The resulting suspension was let to warm up to room temperature and stirred at room temperature overnight (a white suspension formed). The reaction mixture was filtered through a pad of Celite and the filter cake was washed twice with THF. The filtrate was concentrated in vacuo and the residue was dissolved in ethylacetate. The organic phase was extracted with 5 mL aqueous Na2CO3 2M. The organic phase was collected and the aqueous phase was back-extracted with ethylacetate. The combined organic phases were dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a gradient of dichloromethane/methanol to yield the title compound (450 mg, 83%). MS (ESI, m/z): 200.2 (M+H+).

Provenance & Evidence