Pyridine → HCID 21903610, compound

Participants

Reaction Steps

Pyridinium dichloroacetate was prepared in situ by addition of 1.3 equivalents of pyridine (0.49 mL, 6.07 mmol) to dry dichloromethane (4 mL) followed by addition of 1.2 eq. of dichloroacetic acid (0.46 mL, 5.60 mmol). To this mixture was added bisamidite reagent (1.78 mL, 5.60 mmol) followed by the dropwise addition of 2′-deoxy-5′-O-DMT-4-N-benzoylcytidine (2.97 g, 4.67 mmol) dissolved in dry dichloromethane (6 mL). The reaction mixture was stirred under argon at ambient temperature for 2 hours and transferred directly to the top of a short silica gel column. The amidite product was eluted with 70% tOAc/hexanes (1% triethylamine). The appropriate fractions ere collected and evaporated to give 3.47 g (89%) of the title compound as a white foam. 31P NMR (CDCl3) δ 149.29, 149.88.

Provenance & Evidence