Iodine → HCID 68549795, compound

Participants

Reaction Steps

Polymer supported Triphenylphosphine (3 g, 8.38 mmol) was dissolved in 250 mL of DCM followed by addition of I2 (2.13 g, 8.38 mmol) and TEA (3.11 mL, 22.36 mmol) at 0° C. N′-((2R,3S)-3-(tert-butyldimethylsilyloxy)-2-(3-chloro-4-cyano-2-methylphenylamino)butanoyl)-4-(4-methoxybenzyloxy)benzohydrazide (3.56 g, 5.59 mmol) in 200 ml DCM was added to the pre-cooled solution mixture of PPh3/I2/TEA system and stirred. The temperature was allowed to warm to room temperature and stirred for additional 10 minutes. The reaction was quenched with 50 ml saturated sodium thiosulfate and the biphasic mixture was separated. The aqueous layer was extracted with EtOAc (3×80 mL) and the combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure. The resulting crude oil was purified by flash chromatography (SiO2) to provide the title compound (3.02 g, 87%). 1H NMR (400 MHz, Acetone d6, δ in ppm): 7.93 (d, J=9 Hz, 2H), 7.48 (d, J=9 Hz, 1H), 7.43 (d, J=9 Hz, 2H), 7.18 (d, J=9 Hz, 2H), 6.96 (d, J=9 Hz, 2H), 6.83 (d, J=9 Hz, 1H) 5.52 (d, J=9 Hz, 1H), 5.21 (dd, J=2 and 9 Hz, 1H), 5.13 (s, 2H), 4.73 (m, 1H), 3.80 (s, 3H), 2.41 (s, 3H), 1.47 (d, J=6 Hz, 3H), 0.86 (s, 9H), 0.11 (s, 3H), 0.01 (s, 3H).

Provenance & Evidence