Sodium hydride → HCID 131734320, compound

Participants

Reaction Steps

To a solution of 1,4-dioxaspiro[4.5]decan-8-ol (379 mg, 2.40 mmol, 1.20 equiv) in freshly distilled THF (10 mL) was added sodium hydride (60% dispersion in mineral oil, 320 mg, 8.00 mmol, 4.00 equiv) in ice/water bath and stirred for 30 min under nitrogen. A solution of (3S)-3-[[(tert-butyldimethylsilyl)oxy]methyl]-12-chloro-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraene (710 mg, 2.00 mmol, 1.00 equiv) in 10 mL of anhydrous THF was added dropwise and the resulting solution was stirred for 3 h at 60° C. After cooling, the mixture was then quenched with water, extracted with EtOAc (100 mL), dried over anhydrous sodium sulfate. The solvents were evaporated under reduced pressure to obtain (3S)-3-[[(tert-butyldimethylsilyl)oxy]methyl]-12-[1,4-dioxaspiro[4.5]decan-8-yloxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraene (840 mg, 88%) as a yellow oil.

Provenance & Evidence