Trifluoroacetic acid → HCID 22139406, compound

Participants

Reaction Steps

To a solution of [4-(6-Morpholin-4-yl-4-oxo-4H-pyran-2-yl)-9H-thioxanthen-1-yl]-carbamic acid tert-butyl ester (3.25 g) in CH2Cl2 (25 ml) was added trifluoroacetic acid (5 ml). The mixture was stirred at room temperature for 18 hrs whereupon it was cooled (0° C.) and quenched by dropwise addition of saturated NaHCO3 until the pH 9 was attained. The mixture was then extracted using CH2Cl2 (3×20 mL), the combined organic extracts were then dried (MgSO4), filtered and concentrated in vacuo to give a semi-crystalline solid that was applied onto a thin silica pad and eluted with EtOAc (100%) going to EtOAc:MeOH (9:1). The eluent was concentrated in vacuo to give the title compound as a mild amber oil (1.46 g, 56.4% over three steps) m/z (LC-MS, ESP): 393 [M+H]+, R/T=3.79 mins

Provenance & Evidence