Tetrahydrofuran → HCID 22855924, compound

HRID 2399364Notes

Reaction equation

HRID 2399364 reaction equation
[F:1][C@@H:2]1[C@@H:6]([CH2:7]O)[O:5][C@@H:4]([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:3]1.[N+:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[Se:27]C#N)([O-:20])=[O:19].O1CCCC1.C(P(CCCC)CCCC)CCC>C(OCC)(=O)C>[F:1][C@@H:2]1[C@@H:6]([CH2:7][Se:27][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N+:18]([O-:20])=[O:19])[O:5][C@@H:4]([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:3]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 13831TributylphosphineHCID 330393'-FluorothymidineHCID 1039312-Nitrophenyl selenocyanate

Product 1

HCID 22855924HCID 22855924, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3'-Deoxy-3'-fluorothymidine (2.04 g, 8.34 mM) and o-nitrophenylselenocyanate (2.10 g, 9.20 mM) were placed in a flask under nitrogen. Tetrahydrofuran (dry) (50 mL) was added followed by 2.2 mL (8.83 mM) of tri-n-butylphosphine. The mixture was stirred at room temperature for 1.5 hours, diluted with 200 mL of ethyl acetate and washed with 200 mL of sat. sodium bicarbonate followed by 200 mL of brine. The extract was dried over magnesium sulfate and concentrated under reduced pressure to a yellow oil (6.3 g). Chromatographic purification of the yellow oil on silica gel with hexane:ethyl acetate (4:1 v/v) as eluent gave 2.79 g (6.51 mM; 78%) of 3',5'-di-deoxy-3'-fluoro-5'-[(2-nitrophenyl)selenyl]thymidine as an amorphous yellow solid.

Workup

  1. washwashed with 200 mL of sat. sodium bicarbonate
  2. dry with materialThe extract was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure to a yellow oil (6.3 g)
  4. customChromatographic purification of the yellow oil on silica gel with hexane:ethyl acetate (4:1 v/v) as eluent

Sources & evidence

ORD record
ord-8845e437b66c4276a344046351f92475
Source dataset
uspto-grants-1995_09
Patent number
US05449664

Reaction notes

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