Methane → HCID 22792105, compound

HRID 1283377Notes

Reaction equation

HRID 1283377 reaction equation
[C@@H:1]1([N:9]2[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]2=[O:11])[O:6][C@H:5]([CH2:7][OH:8])[CH2:4][C@@H:2]1[OH:3].N1C=CC=CC=1.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1.C>C(O)C>[S:29]([O:8][CH2:7][C@H:5]1[O:6][C@@H:1]([N:9]2[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]2=[O:11])[C@@H:2]([OH:3])[CH2:4]1)([C:26]1[CH:27]=[CH:28][C:23]([CH3:33])=[CH:24][CH:25]=1)(=[O:31])=[O:30]

Participants

6

Reactant 4

HCID 297MethaneHCID 1049Pyridine2×HCID 73974-Toluenesulfonyl chlorideHCID 14444899HCID 14444899, compound

Product 1

HCID 22792105HCID 22792105, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

With moisture excluded, a solution consisting of 228 mg. (1.0 millimoles) of 1-(3-deoxy-β-D-threopentofuranosyl)-uracil [Prepared according to the method described by Horwitz et al., J. Org. Chem. 31, pp. 205--211 (1966)] and 2.5 ml. pyridine was chilled to 0° C. and a solution consisting of 236 mg. (1.24 millimoles) p-toluenesulfonyl chloride and 2.5 ml. pyridine was added dropwise while the temperature of the reaction mixture was maintained at 0° C. The reaction vessel was securely sealed and set aside at 3° to 5° C. for about 16 hrs. Afterwards, a small portion of crushed ice was added to the reaction mixture and refrigeration was continued for about 1 to 2 hrs. This mixture was further diluted with 50 ml. of ice-cold water and the dilute aqueous solution was extracted three times with 30 ml. portions of chloroform. The chloroform extracts were combined and dried over anhydrous sodium sulfate. After removing the chloroform by evaporation under reduced pressure, the residue thus obtained was dissolved in hot absolute ethanol. Some decolorizing charcoal was added to the ethanol solution, the charcoal was removed by filtration, and the filter was washed with hot absolute ethnol. The ethanol was removed from the combined filtrate and washings under reduced pressure, and the residue thus obtained was azeotroped with absolute ethanol under reduced pressure. There was thus obtained 182.8 mg. of 1-(5-O-tosyl- 3-deoxy-β-D-threopentofuranosyl)uracil as an amorphous solid.

Workup

  1. customThe reaction vessel was securely sealed
  2. additionAfterwards, a small portion of crushed ice was added to the reaction mixture and refrigeration
  3. waitwas continued for about 1 to 2 hrs
  4. additionThis mixture was further diluted with 50 ml
  5. extractionof ice-cold water and the dilute aqueous solution was extracted three times with 30 ml
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter removing the chloroform
  8. customby evaporation under reduced pressure
  9. customthe residue thus obtained
  10. customthe charcoal was removed by filtration
  11. washthe filter was washed with hot absolute ethnol
  12. customThe ethanol was removed from the combined filtrate and washings under reduced pressure
  13. customthe residue thus obtained
  14. customwas azeotroped with absolute ethanol under reduced pressure

Sources & evidence

ORD record
ord-146462075c464000b934ed700ab28668
Source dataset
uspto-grants-1976_08
Patent number
US03975374

Reaction notes

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