Tetrabutylammonium Fluoride → tert-butyl N-(4-[[(12R)-12-(2-hydroxyethyl)-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-3-yl]oxy]cyclohexyl)carbamate

Participants

Reaction Steps

To a solution of tert-butyl N-(4-[[(12R)-12-[2-[(tert-butyldimethylsilyl)oxy]ethyl]-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2 (7),3,5-tetraen-3-yl]oxy]cyclohexyl)carbamate (200 mg, 0.36 mmol, 1.00 equiv) in 6 mL of THF was added TBAF (186 mg, 0.71 mmol, 2.00 equiv) at room temperature and the resulting solution was stirred overnight at ambient temperature. The reaction was then quenched with water, extracted with 3×30 mL of ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. Purification by column chromatography on silica gel with ethyl acetate/petroleum ether (1:2) afford 129 mg (81%) of the desired tert-butyl N-(4-[[(12R)-12-(2-hydroxyethyl)-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-3-yl]oxy]cyclohexyl)carbamate as a yellow oil.

Provenance & Evidence