Thymidine → HCID 69967848, compound

HRID 356728Notes

Reaction equation

HRID 356728 reaction equation
[C@@H:1]1([N:9]2[CH:17]=[C:15]([CH3:16])[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.[N+:18]([C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1)([O-:20])=[O:19].C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[N+:18]([C:21]1[CH:22]=[CH:23][C:24]([C:25]([C@@:1]2([N:9]3[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]3=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]2)=[O:26])=[CH:28][CH:29]=1)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 5789ThymidineHCID 85024-Nitrobenzoyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 69967848HCID 69967848, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

Thymidine (2.42 g; 10 mmol) is dried by coevaporation in pyridine, then taken up in 200 ml of anhydrous pyridine and cooled to 4° C. p-Nitrobenzoyl chloride (2.04 g; 11 mmol) is added. The temperature is allowed to rise and the reaction is left overnight at room temperature. The reaction is stopped with 5 ml of saturated sodium bicarbonate. The reaction mixture is concentrated and then taken up in 500 ml of chloroform. The organic solution obtained is washed with 2×500 ml of 0.5M NaHCO3 and then with 250 ml of saturated NaCl. The aqueous phases are counter-extracted with 100 ml of CHCl3. The organic phases are evaporated. The pure product is obtained by column chromatography on silica. It is eluted with 5% of methanol in chloroform. Yield=58%.

Workup

  1. additionis added
  2. concentrationThe reaction mixture is concentrated
  3. customThe organic solution obtained
  4. washis washed with 2×500 ml of 0.5M NaHCO3
  5. extractionThe aqueous phases are counter-extracted with 100 ml of CHCl3
  6. customThe organic phases are evaporated
  7. customThe pure product is obtained by column chromatography on silica
  8. washIt is eluted with 5% of methanol in chloroform

Sources & evidence

ORD record
ord-9b58cf7788b34235a64633e0d28afbf9
Source dataset
uspto-grants-1998_11
Patent number
US05837859

Reaction notes

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