(Diethylamino)sulfur trifluoride → HCID 58466231, compound

Participants

Reaction Conditions

Reaction Steps

To a RBF was added (S)-3-(2-amino-5′-fluoro-2′-methoxy-5H-spiro[oxazole-4,9′-xanthene]-7′-yl)oxetan-3-ol (0.28 g, 0.75 mmol, prepared as described in Method CCl4) and DCM (5 mL). The resulting mixture was then cooled to 0° C. and (diethylamino)sulfur trifluoride (0.20 mL, 1.50 mmol, Alfa Aesar) was added drop wise. The mixture was then stirred at 0° C. for 15 min and at room temperature for 15 min. Then, the mixture was quenched with saturated sodium bicarbonate (5 mL). The mixture was stirred at 0° C. for 5 min and at RT for 5 min. Then, the organic layer was collected and the aqueous layer was extracted with DCM (1×10 mL). The combined organic extracts were dried over MgSO4 and silica gel was added. The solvent was removed and the solid mixture was purified by silica gel flash column chromatography using ISCO instrument (solid loading, 20-100% EtOAc/hexane) to give the title compound as a white solid. MS (ESI, positive ion) m/z: 375 (M+H).

Provenance & Evidence