Pyridine → HCID 10579640, compound

HRID 660001Notes

Reaction equation

HRID 660001 reaction equation
[CH2:1]([O:8][C@@H:9]1[C:13]([CH2:20][O:21][S:22]([CH3:25])(=[O:24])=[O:23])([CH2:14][O:15][S:16]([CH3:19])(=[O:18])=[O:17])[O:12][C@@H:11]([N:26]2[CH:34]=[C:32]([CH3:33])[C:30](=[O:31])[NH:29][C:27]2=[O:28])[C@@H:10]1[OH:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:42][S:43](Cl)(=[O:45])=[O:44]>ClCCl>[CH2:1]([O:8][C@@H:9]1[C:13]([CH2:14][O:15][S:16]([CH3:19])(=[O:17])=[O:18])([CH2:20][O:21][S:22]([CH3:25])(=[O:24])=[O:23])[O:12][C@@H:11]([N:26]2[CH:34]=[C:32]([CH3:33])[C:30](=[O:31])[NH:29][C:27]2=[O:28])[C@@H:10]1[O:35][S:43]([CH3:42])(=[O:45])=[O:44])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 13008799HCID 13008799, compound

Product 1

HCID 10579640HCID 10579640, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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)

Workup

  1. customAfter 2 h the reaction was quenched with sat. aq NaHCO3 (200 mL)
  2. customthe phases were separated
  3. extractionThe aq phase was extracted with dichloromethane (2×150 mL)
  4. washthe combined organic phases were washed with aq HCl (1 M, 2×200 mL), sat. aq NaHCO3 (2×250 mL) and brine (250 mL)
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ab08db35b72944a1a33672142c90ae7c
Source dataset
uspto-grants-2011_12
Patent number
US08084458B2

Reaction notes

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