Acetyl Protection

(Acetyl Chloride)

Examples:

Example 1

To a mixture of the SM (65 mg, 0.22 mmol) and TEA (67 mg, 0.66 mmol) in THF (5 mL) was added acetyl chloride (34 mg, 0.44 mmol) at RT. The reaction mixture was stirred at RT for 3 h. After concentration, the residue was purified by Prep HPLC to provide the product as a white solid. [52 mg, 70%]

[Patent Reference: WO2016011390, page 63, (20.2 MB)]

Example 2

To a mixture of the SM (95 mg, 0.28 mmol) and TEA (86 mg, 0.84 mmol) in THF (5 mL) was added acetyl chloride (44 mg, 0.56 mmol). The reaction mixture was stirred at RT for 1 h. The mixture was concentrated and the resulting residue was purified by Prep HPLC [5-95% (ACN)/(H2O with 0.05% TFA)] to provide the product as a white solid. [65 mg, 61%]

[Patent Reference: WO2016011390, page 170, (20.2 MB)]