Triethylamine → 3-benzoyl-2'-deoxy-3',5'-di-O-acetyl-5-fluorouridine

HRID 745656Notes

Reaction equation

HRID 745656 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11][C:12](=[O:14])[CH3:13])[O:8][C@@H:7]([N:15]2[CH:22]=[C:21]([F:23])[C:19](=[O:20])[NH:18][C:16]2=[O:17])[CH2:6]1)(=[O:3])[CH3:2].C(N(CC)CC)C.[C:31](Br)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>O1CCOCC1>[C:31]([N:18]1[C:19](=[O:20])[C:21]([F:23])=[CH:22][N:15]([C@@H:7]2[O:8][C@H:9]([CH2:10][O:11][C:12](=[O:14])[CH3:13])[C@@H:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:6]2)[C:16]1=[O:17])(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12056Benzoyl bromideHCID 127901643',5'-Di-O-acetyl-2'-deoxy-5-fluorouridine

Product 1

HCID 228287873-benzoyl-2'-deoxy-3',5'-di-O-acetyl-5-fluorouridineYield 60.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

500 mg of 2'-deoxy-3',5'-di-O-acetyl-5-fluorouridine and 0.76 ml of triethylamine were dissolved in 10 ml of dry dioxane, and the resulting mixture was cooled with ice. To the mixture was added 850 mg of benzoyl bromide, and the resulting mixture was allowed to stand at room temperature for 15 minutes and then at 70° C. for 30 minutes. The same procedure as in Example 8 gave 400 mg (yield: 60.5%) of 3-benzoyl-2'-deoxy-3',5'-di-O-acetyl-5-fluorouridine. The absorption spectra of the present product were identical with those of the compound obtained in Example 8.

Workup

  1. temperaturethe resulting mixture was cooled with ice
  2. waitat 70° C. for 30 minutes

Sources & evidence

ORD record
ord-df7060b2176247bf92466a52c925e2b9
Source dataset
uspto-grants-1986_07
Patent number
US04599404

Reaction notes

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