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SEM Deprotection



Example 1

A mixture of the SM (0.11 g, 0.33 mmol), EtOH (0.5 mL), and conc HCl (0.5 mL) was heated at about 80 C overnight. The mixture was concentrated to dryness and to the resulting residue was added sat aq NaHCO3. The mixture was extracted with 25% IPA/Chloroform. The org layer was washed with brine and concentrated in vacuo to provide the product as a yellow solid. [0.060 g, 87%] [WO2012149280, page 77]

Example 2

To a stirring solution of the SM (75 mg, 0.107 mmol) in dioxane (2 mL) was added 12M HCl (0.5 mL). The reaction mixture was stirred at 80 C for 2 h, after which time the solvent was removed in vacuo. The residue was dissolved in dioxane (2 mL) and NH4OH (0.5 mL) was added. The mixture was stirred at RT for 2 h. The solvent was removed in vacuo and the resulting material was purified by reverse phase column chromatography (C18 silica gel, 70% ACN/H2O as eluent) to provide the product as a white solid. [10 mg, 16%] [WO2015129926, page 248]