Triacetoxyperiodinane → HCID 89544846, compound

Participants

Reaction Steps

Step 2 Dess-Martin periodinane (243 mg, 0.572 mmol) was dissolved in dry CH2Cl2 (1 mL) and then added dropwise to a solution of tert-butyl N-[(1R)-1-(4-chloro-2-fluoro-3-{hydroxy[2-(methylsulfanyl)pyrimidin-5-yl]methyl}phenyl)propyl]carbamate (194 mg, 0.439 mmol) in dry CH2Cl2 (1 mL) and the solution was stirred at rt for 8 h. After this time the reaction mixture was diluted with CH2Cl2 (10 mL) and washed with saturated NaHCO3 (10 mL). The aqueous phase was extracted with CH2Cl2 (3×10 mL) and the combined organic extracts were washed with saturated Na2SO3 (10 mL) and brine (10 mL), dried (Na2SO4), filtered and concentrated in vacuo to give crude material (˜200 mg). Purified by silica column (25M on Biotage SP4) eluting 20-40% EtOAc in petroleum ether over 15 column volumes to give tert-butyl N-[(1R)-1-(4-chloro-2-fluoro-3-{[2-(methylsulfanyl)pyrimidin-5-yl]carbonyl}phenyl)propyl]-carbamate (100 mg, 0.23 mmol, 0.52%). m/z: 439.

Provenance & Evidence