Benzoyl chloride → HCID 86745211, compound

HRID 973793Notes

Reaction equation

HRID 973793 reaction equation
[C:1]([CH:4]([OH:22])[C@H:5]1[O:9][C@@H:8]([N:10]2[CH:18]=[C:16]([CH3:17])[C:14](=[O:15])[NH:13][C:11]2=[O:12])[CH2:7][C@@H:6]1[N:19]=[N+:20]=[N-:21])(=[O:3])[CH3:2].[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>N1C=CC=CC=1>[C:1]([CH:4]([OH:22])[C@H:5]1[O:9][C@@H:8]([N:10]2[CH:18]=[C:16]([CH3:17])[C:14](=[O:15])[N:13]([C:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:11]2=[O:12])[CH2:7][C@@H:6]1[N:19]=[N+:20]=[N-:21])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 86745212HCID 86745212, compound

Product 1

HCID 86745211HCID 86745211, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5'-Acetyl-3'-azido-3'-deoxythymidine (0.75 g, 2.4 mMol) was dissolved in pyridine (5 mL) and benzoyl chloride (1.4 mL, 12 mMol, 5 eq.) was added at room temperature. The reaction was stirred overnight then poured onto ice water (250 mL). The pH of the aqueous solution was adjusted to 1. The product was extracted with chloroform. The organic phase was washed with water, dried with MgSO4 and filtered. The chloroform was removed and the oily product was flash chromatographed on silica gel eluted with chloroform. The product was collected as an oil.

Workup

  1. additionthen poured onto ice water (250 mL)
  2. extractionThe product was extracted with chloroform
  3. washThe organic phase was washed with water
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customThe chloroform was removed
  7. customchromatographed on silica gel
  8. washeluted with chloroform
  9. customThe product was collected as an oil

Sources & evidence

ORD record
ord-f6f9a94888b5495d90d674142a2d2836
Source dataset
uspto-grants-1991_11
Patent number
US05064946

Reaction notes

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