Benzoyl chloride → 1-[4-Benzoyloxy-3-(benzoyloxymethyl)-1-butyl]-5-vinyluracil

HRID 732926Notes

Reaction equation

HRID 732926 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:10][CH2:11][CH:12]([CH2:25][OH:26])[CH2:13][CH2:14][N:15]1[CH:22]=[C:21]([CH:23]=[CH2:24])[C:19](=[O:20])[NH:18][C:16]1=[O:17]>N1C=CC=CC=1>[C:1]([O:10][CH2:11][CH:12]([CH2:25][O:26][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:13][CH2:14][N:15]1[CH:22]=[C:21]([CH:23]=[CH2:24])[C:19](=[O:20])[NH:18][C:16]1=[O:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 100372831-[4-Hydroxy-3-(hydroxymethyl)-1-butyl]-5-vinyluracil

Product 1

HCID 110915841-[4-Benzoyloxy-3-(benzoyloxymethyl)-1-butyl]-5-vinyluracilYield 65.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzoylchloride (600 mg, 4.2 mmol) was added to a solution of 20 (450 mg, 1.87 mmol) in dry pyridine (50 ml) and the reaction was allowed to proceed at 25° C. with stirring for 48 h. The reaction mixture was poured onto ice water (50 ml) and extracted with dichloromethane (3×50 ml). The dichloromethane extract was dried over sodium sulfate, the solvent was removed in vacuo and the residue obtained was purified by elution from a silica gel column using chloroform-methanol (97:3, v/v) as eluent to yield 22 as a viscous oil (550 mg, 65.4%) which was used directly in the next reaction step.

Workup

  1. customto proceed at 25° C.
  2. additionThe reaction mixture was poured onto ice water (50 ml)
  3. extractionextracted with dichloromethane (3×50 ml)
  4. extractionThe dichloromethane extract
  5. dry with materialwas dried over sodium sulfate
  6. customthe solvent was removed in vacuo
  7. customthe residue obtained
  8. customwas purified by elution from a silica gel column

Sources & evidence

ORD record
ord-41e1be21bf4a4ce3b5532f1bc5d1a1ff
Source dataset
uspto-grants-2009_09
Patent number
US07589077B2

Reaction notes

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