Acid to Ester

(DCC + DMAP)

Examples:

Example 1

To a solution of the SM (10.0 g, 65.3 mmol) in DCM (400 mL) was added t-butanol (15.6 mL, 163 mmol), DCC (21.6 g, 104 mmol), and DMAP (16.0 g, 131 mmol). The reaction mixture was stirred at RT for 3 days. The solids were filtered away and the filtrate was concentrated in vacuo. The crude material was purified by silica gel flash chromatography, then triturated with 10% EtOAc/heptane. The solids were filtered away and the filtrate was concentrated in vacuo to provide the product. [9.7 g, 70%]

[Patent Reference: WO2016014463, page 72, (6.7 MB)]

Example 2

To a solution of the SM (200 g, 0.851 mol) in DCM (6.0 L) at 0 C was added t-butanol (158 g, 2.13 mol), DMAP (52.0 g, 0.425 mol) and EDCI (163 g, 0.853 mol). The reaction mixture was stirred at RT overnight. Next, the reaction mixture was concentrated and the residue dissolved in EtOAc. The org layer was washed with 10% aq citric acid, 10% aq NaHCO3, brine, dried (Na2SO4), and concentrated to provide the product as a colorless oil. [200 g, 81%]

[Patent Reference: WO2011017578, page 126, (8.3 MB)]