Isophthaloyl chloride → 5'-O-acetyl-3-[3-(4-benzoyloxy-5-chloro-2-pyridyloxycarbonyl)benzoyl]-3'-O-benzyl-2'-deoxy-5-fluorouridine

HRID 703550Notes

Reaction equation

HRID 703550 reaction equation
[C:1]([O:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[CH:18]=[C:17]([F:19])[C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:8][C@@H:7]1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:3])[CH3:2].[C:28](Cl)(=[O:38])[C:29]1[CH:37]=[CH:36][CH:35]=[C:31]([C:32](Cl)=[O:33])[CH:30]=1.C(N(CC)CC)C.[C:47]([O:55][C:56]1[C:61]([Cl:62])=[CH:60][NH:59][C:58](=[O:63])[CH:57]=1)(=[O:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>O1CCOCC1>[C:1]([O:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[CH:18]=[C:17]([F:19])[C:15](=[O:16])[N:14]([C:28](=[O:38])[C:29]3[CH:37]=[CH:36][CH:35]=[C:31]([C:32]([O:63][C:58]4[CH:57]=[C:56]([O:55][C:47](=[O:54])[C:48]5[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=5)[C:61]([Cl:62])=[CH:60][N:59]=4)=[O:33])[CH:30]=3)[C:12]2=[O:13])[CH2:8][C@@H:7]1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 7451Isophthaloyl chlorideHCID 8471Triethylamine2×HCID 136874845'-O-acetyl-3'-O-benzyl-2'-deoxy-5-fluorouridineHCID 140496465-Chloro-2-oxo-1,2-dihydropyridin-4-yl benzoate

Product 1

HCID 186348145'-O-acetyl-3-[3-(4-benzoyloxy-5-chloro-2-pyridyloxycarbonyl)benzoyl]-3'-O-benzyl-2'-deoxy-5-fluorouridineYield 37.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.60 g of 5'-O-acetyl-3'-O-benzyl-2'-deoxy-5-fluorouridine in 30 ml of dry dioxane were added 0.42 g of isophthaloyl chloride and 1.11 ml of triethylamine, and the mixture was refluxed for 2 hours. Then 0.60 g of 4-benzoyloxy-5-chloro-2(1H)-pyridone and 1.11 ml of triethyl amine were added and the resulting mixture was refluxed for 1 hour. The precipitate thus formed was filtered off, and the filtrate was concentrated. The residue was placed on a silica gel column and eluted with 40% ethyl acetate-benzene, giving 0.45 g of the title compound in a yield of 37%.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperaturethe resulting mixture was refluxed for 1 hour
  3. customThe precipitate thus formed
  4. filtrationwas filtered off
  5. concentrationthe filtrate was concentrated
  6. washeluted with 40% ethyl acetate-benzene

Sources & evidence

ORD record
ord-ba9781ca37d84e488918675ad90467f5
Source dataset
uspto-grants-1991_01
Patent number
US04983609

Reaction notes

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