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Curtius Rearrangement

(Cbz Protected Pdt)


Example 1

DPPA (1.73 mL, 8.04 mmol) was added to a solution of the SM (1.45 g, 7.31 mmol) and TEA (1.02 mL, 7.31 mmol) in toluene (15 mL). The mixture was stirred at 90 C for 2 h. Then, benzyl alcohol (0.75 mL, 7.31 mmol) was added and the reaction mixture was stirred at 90 C for 4 days. The mixture was cooled to RT, diluted with EtOAc, and washed with sat aq NaHCO3. The org layer was separated, dried, and concentrated to give a residue that was purified by chromatography (0-20% EtOAc/heptane) to provide the product. [1.78 g, 5.86 mmol]

[Patent Reference: WO2016020526, page 58, (5.6 MB)]