4-Toluenesulfonyl chloride → HCID 11036334, compound

HRID 1974220Notes

Reaction equation

HRID 1974220 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:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>N1C=CC=CC=1>[S:23]([O:7][CH2:6][C@H:5]1[O:8][C@@H:1]([N:9]2[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:2][C@@H:3]1[OH:4])([C:20]1[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=1)(=[O:25])=[O:24]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 13712Deoxyuridine

Product 1

HCID 11036334HCID 11036334, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

22.8 GM OF DEOXYURIDINE (100 MMOLES) ARE DISSOLVED IN 100 ML OF FRESHLY DISTILLED, DRY PYRIDINE AND KEPT ON ICE AT 4° C. Freshly recrystallized p-toluenesulfonyl chloride (22 gm, 115 mmoles) is dissolved in a separate 100 ml of cold pyridine and then slowly added to the nucleoside solution. The reaction mixture is left standing at 4° C for 24 hours and the solution poured into 400 ml of ice water. This solution is then extracted twice with 500 ml of chloroform, the chloroform extracts combined and back extracted with 250 ml of a saturated solution of sodium bicarbonate and 250 ml of water. The chloroform layer is collected and dried over anhydrous magnesium sulfate. The solvent is removed by rotary evaporation in vacuo to yield 32 gm of a crude, tan-colored product. Recrystallization from 95% ethanol affords 25.3 gm (66% yield) of white crystals, M.P. 162°.

Workup

  1. distillationOF FRESHLY DISTILLED
  2. customON ICE AT 4° C
  3. waitThe reaction mixture is left
  4. extractionThis solution is then extracted twice with 500 ml of chloroform
  5. extractionback extracted with 250 ml of a saturated solution of sodium bicarbonate and 250 ml of water
  6. customThe chloroform layer is collected
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent is removed by rotary evaporation in vacuo
  9. customto yield 32 gm of a crude, tan-colored product
  10. customRecrystallization from 95% ethanol

Sources & evidence

ORD record
ord-d53805771f9b4c56a25008f9b7f71333
Source dataset
uspto-grants-1976_12
Patent number
US04000260

Reaction notes

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