Sodium hydride → HCID 86695200, compound

Participants

Reaction Steps

To a solution of tert-butyl N-(4-hydroxy-1-methylcyclohexyl)carbamate (700 mg, 3.05 mmol, 1.00 equiv) in anhydrous THF (10 mL) was added sodium hydride (60% dispersion in mineral oil, 600 mg, 15.00 mmol, 4.91 equiv) at 0° C. under nitrogen. The resulting solution was stirred for 0.5 h at room temperature. To this was added (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 (1.18 g, 3.32 mmol, 1.09 equiv) and stirring was continued for 5 h at 30° C. The reaction was then quenched by the addition of 30 mL of NH4Cl (aq.) and extracted with 3×80 mL of ethyl acetate. The organic phase was dried over sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/15) to yield 1.20 g (72%) of tert-butyl N-(4-[[(3S)-3-[[(tert-butyldimethylsilyl)oxy]methyl]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]-1-methylcyclohexyl)carbamate as a light yellow solid.

Provenance & Evidence