Tetrahydrofuran → 3-((3',4'-Dihydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-8'-yl)methyl)-N-(2,4-dimethoxybenzyl)-5-fluoro-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide

Participants

Reaction Steps

To a flask containing N-(2,4-Dimethoxybenzyl)-5-fluoro-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydro-1,3-benzoxazole-6-sulfonamide (11-3) (2.13 g, 4.57 mmol), resin bound (PS) TRIPHENYLPHOSPHINE (5.27 g, 9.70 mmol) & DTBAD (2.187 g, 9.50 mmol) & (3′,4′-dihydro-1′H-spiro[[1,3]dioxolane-2,2′-naphthalen]-8′-yl)methanol (19-3) (1.162 g, 5.28 mmol) was added anhydrous THF (40 ml). The reaction mixture was then capped (not under N2) & stirred at room temperature for ˜16 hours (overnight). Followed by LC/MS. The reaction mixture was diluted with DCM/EtOAc, filtered (to remove the resin), it was noticed that the filtrate was cloudy white so it was filtered to yield 3-((3′,4′-dihydro-1′H-spiro[[1,3]dioxolane-2,2′-naphthalen]-8′-yl)methyl)-N-(2,4-dimethoxybenzyl)-5-fluoro-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide (19-4).

Provenance & Evidence