Cornforth reagent → HCID 86695170, compound

Participants

Reaction Steps

To a solution of tert-butyl N-(4-[[(12S)-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 (172 mg, 0.38 mmol, 1.00 equiv) in 4 mL of DMF was added PDC (847 mg, 2.25 mmol, 6.00 equiv) and the resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of water and extracted with 4×50 mL of chloroform/isopropanol (3:1). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:1) to provide 2-[(12S)-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-12-yl]acetic acid (148 mg, 83%) as an off-white solid. MS: m/z 462 (M+H)+.

Provenance & Evidence