Pyridine → HCID 10579640, compound

Participants

Reaction Conditions

Reaction Steps

Nucleoside 27 (20 g, 37 mmol) was dissolved in anhyd dichloromethane (100 mL) and anhyd pyridine (100 mL) was added. The solution was cooled to 0° C. and methanesulfonyl chloride (4.4 mL, 56 mmol) was added dropwise. After 2 h the reaction was quenched with sat. aq NaHCO3 (200 mL), and the phases were separated. The aq phase was extracted with dichloromethane (2×150 mL), and the combined organic phases were washed with aq HCl (1 M, 2×200 mL), sat. aq NaHCO3 (2×250 mL) and brine (250 mL). The organic phase was dried (Na2SO4), filtered and the solvent was removed in vacuo. The crude product was co-evaporated with toluene affording 28 (22 g, 96%) as a white foam. Rf=0.41 (100% EtOAc); ESI-MS m/z found 635.0 ([MNa]+, calcd 635.1). All analytical data were identical to those previously reported. (Håkansson, A. E.; Koshkin, A.; Sørensen, M. D.; Wengel, J. J. Org. Chem. 2000, 65, 5161-5166)

Provenance & Evidence