Sodium Azide → HCID 117600285, compound

Participants

Reaction Conditions

Reaction Steps

A resealable vessel was flushed with argon and loaded with copper(I) iodide (0.138 g, 0.726 mmol), sodium azide (0.708 g, 10.90 mmol), and sodium (R)-2-((S)-1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydrofuran-3-olate (0.072 g, 0.363 mmol). A solution of (S)-7′-bromo-4′-fluoro-2′-methoxy-5,6-dihydrospiro[[1,3]oxazine-4,9′-xanthen]-2-amine (1.428 g, 3.63 mmol) in dmso (20 mL) was degassed and transferred via cannula into the resealable vessel. Water (4 mL) was added. The vessel was flushed with argon, and (1R,2R)—N1,N2-dimethylcyclohexane-1,2-diamine (0.163 mL, 1.090 mmol) was added. The vessel was sealed and heated in a 90° C. oil bath. After 4 h, the reaction mixture was taken up in EtOAc (600 mL) and the organic layer was extracted with quarter-saturated brine (2×70 mL), half-saturated brine (70 mL), and saturated brine (70 mL), dried over MgSO4 and concentrated to afford crude (S)-7′-azido-4′-fluoro-2′-methoxy-5,6-dihydrospiro[[1,3]oxazine-4,9′-xanthen]-2-amine, which was used without purification in the next step. MS m/z=356 [M+H]+.

Provenance & Evidence