Water → HCID 178518758, compound

HRID 1086950Notes

Reaction equation

HRID 1086950 reaction equation
[F:1][C:2]1[C:3](=[O:17])[NH:4][C:5](=[O:16])[N:6]([CH:15]=1)[C@@H:7]1[O:14][C@H:11]([CH2:12][OH:13])[C@@H:9]([OH:10])[CH2:8]1.C(C1C=C(C(C)C)C=C(C(C)C)C=1S(Cl)(=O)=O)(C)C.C1([NH3+])CCCCC1.[C:44]1([S-:50]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[P:51](=[S:54])([O-])[O-:52])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.C1([NH3+])CCCCC1.C1([NH3+])CCCCC1.O>N1C=CC=CC=1>[C:44]1([SH:50]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[P:51]([O:13][CH2:12][C@H:11]2[O:14][C@@H:7]([N:6]3[CH:15]=[C:2]([F:1])[C:3](=[O:17])[NH:4][C:5]3=[O:16])[CH2:8][C@@H:9]2[OH:10])(=[S:54])[OH:52])[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5790FloxuridineHCID 810422,4,6-Tris(1-methylethyl)benzenesulfonyl chlorideHCID 178514184HCID 178514184, compound

Product 1

HCID 178518758HCID 178518758, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 500 mg (2.03 mmol) of 2'-deoxy-5-fluorouridine in 5 ml of pyridine was cooled to -10° C. to 0° C. in an ice-water bath. To this solution was added dropwise a mixture of 1.00 g (3.30 mmol) of 2,4,6-triisopropylbenzenesulfonylchloride, 1.36 g (3.56 mmol) of S,S-diphenylphosphorodithioate monocyclohexylammonium and 5 ml of pyridine over the period of 10 minutes. After the completion of the dropwise addition, the mixture was stirred at room temperature overnight. To this reaction mixture was added 100 ml of water. The mixture was extracted with 10 ml of chloroform repeatedly three times. The extract was washed with an aqueous solution of dilute hydrochloric acid and water in order, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure The obtained residue was subjected to silica gel column chromatography with the use of a mixture of chloroform and methanol (9:1 v/v) as the eluent to give 599 mg of 2'-deoxy-5-fluorouridine 5'-(S,S-diphenylphosphorodithioate) in a glassy form (Yield 55%).

Workup

  1. additionTo this solution was added dropwise
  2. additionAfter the completion of the dropwise addition
  3. extractionThe mixture was extracted with 10 ml of chloroform repeatedly three times
  4. washThe extract was washed with an aqueous solution of dilute hydrochloric acid and water in order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure The obtained residue
  7. additionwas subjected to silica gel column chromatography with the use of a mixture of chloroform and methanol (9:1 v/v) as the eluent

Sources & evidence

ORD record
ord-c4ec1509464c4847a8c6c66f0e455347
Source dataset
uspto-grants-1991_07
Patent number
US05032680

Reaction notes

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