Iodine → HCID 66928527, compound

Participants

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-(2-tert-butoxycarbonylamino-acetylamino)-3-hydroxy-3-phenyl-propionic acid methyl ester (620 mg, 1.76 mmol) in CH2Cl2 (20.0 mL) was treated at 0° C. with Dess-Martin periodinane (923 mg, 2.11 mmol). The resulting mixture was stirred at rt for 1 h and filtered through a short plug of basic alumina (activity I) and sand into a flask containing a freshly prepared solution of triphenylphosphine (946 mg, 3.55 mmol), I2 (902 mg, 3.52 mmol) and Et3N (0.98 ml, 7.04 mmol) in CH2Cl2 (22.0 mL). The filter cake was washed with CH2Cl2. After 15 min, the reaction mixture was transferred to a separatory funnel, treated with sat. aq. Na2S2O3 (150 mL) and extracted with CH2Cl2 (2×150 mL). The organic layer was washed with sat. aq. NaHCO3 (150 mL), filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (50:50 CH2Cl2-MeOH) gave the title compound as a white solid. TLC: rf (50:50 CH2Cl2-MeOH)=0.33. LC-MS-conditions 02: tR=0.99 min, [M+H]+=333.39.

Provenance & Evidence