HCID 86695200, compound → HCID 86695201, compound

Participants

Reaction Steps

To a solution 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 (1.20 g, 2.19 mmol, 1.00 equiv) in tetrahydrofuran (15 mL) was added TBAF-3H2O (1.09 g, 3.45 mmol, 1.58 equiv) at 0° C. and the resulting solution was stirred for 3 h at room temperature. The reaction was quenched with water and extracted with 3×100 mL of ethyl acetate. The organic layers were washed with brine, dried over sodium sulfate and concentrated under vacuum. Purification by column chromatography on silica gel with ethyl acetate/petroleum ether (1:20 to 1:5) afforded tert-butyl N-(4-[[(3S)-3-(hydroxymethyl)-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 (900 mg, 95%) as a colorless oil.

Provenance & Evidence