Cbz Protection

(Succinimidyl Reagent)

Examples:

Example 1

To a solution of the SM (30.5 g, 148.6 mmol) in THF/H2O (1:1, 400 mL) was added NaHCO3 (24.7 g, 294 mmol), followed by benzyl N-succinimidyl carbonate (44.0 g, 176 mmol) at RT. The reaction was stirred at RT for 4 h, after which time the layers were separated and the aq layer was further extracted with EtOAc (2x). The combined organics were washed with brine, dried (MgSO4), concentrated, and purified by silica gel chromatography (0-60% EtOAc/hexane) to provide the product as a yellow oil. [44.8 g, 89%]

[Patent Reference: WO2011123693, page 70, (11.9 MB)]