Sodium hydride → HCID 86695225, compound

Participants

Reaction Conditions

Reaction Steps

NaH (60% dispersion in mineral oil, 438 mg, 10.95 mmol, 4.00 equiv) was treated with tert-butyl N-(4-hydroxycyclohexyl)carbamate (710 mg, 3.30 mmol, 1.20 equiv) in freshly distilled THF at 50° C. for 30 min under nitrogen. Then a solution of ethyl 2-[(13S)-3-chloro-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-13-yl]acetate (850 mg, 2.73 mmol, 1.00 equiv) in THF (10 mL) was added via syringe and stirred for 2 h at 60° C. After cooling, the reaction was quenched with brine, extracted with ethyl acetate (80 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5) to give 800 mg (60%) of ethyl 2-[(13S)-3-[(4-[[(tert-butoxy)carbonyl]amino]cyclohexyl)oxy]-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-13-yl]acetate as a colorless oil.

Provenance & Evidence