Trimethylsilyl triflate → HCID 57867381, compound

HRID 1516257Notes

Reaction equation

HRID 1516257 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.N12CCCN=[C:17]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[C:34]([O:42][CH2:43][C@@H:44]1[C@@:48]([O:50][C:51](=[O:53])C)([CH3:49])[C@:47]([F:55])([CH3:54])[CH:46](OC(=O)C)[O:45]1)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(#N)C>[C:34]([O:42][CH2:43][C@@H:44]1[C@@:48]([O:50][C:51](=[O:53])[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([CH3:49])[C@:47]([F:55])([CH3:54])[CH:46]([N:6]2[CH:5]=[N:4][C:3]3[C:7]2=[N:8][CH:9]=[N:10][C:2]=3[Cl:1])[O:45]1)(=[O:41])[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 65367Trimethylsilyl triflateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 53592776-ChloropurineHCID 68981036HCID 68981036, compound

Product 1

HCID 57867381HCID 57867381, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a stirred solution of 6-chloropurine (about 0.26 g, 1.74 mmol) in Acetonitrile (about 8 ml) was added 1,8-Diazabicyclo[5.4.0]undec-7-ene (about 0.52 ml, 3.48 mmol) and Trimethylsilyl trifluoromethanesulfonate (about 0.84 ml, 4.65 mmol) at about 0° C., stirred for about 15 minutes then ((2R,3S,4R)-3,5-diacetoxy-4-fluoro-3,4-dimethyl-tetrahydrofuran-2-yl)methyl benzoate (about 0.5 g, 1.16 mmol) in Acetonitrile (about 7 ml) was added and reaction continued stirring at about 65° C. for about 8 hours. Completion of reaction monitored by thin-layer chromatography and quenched with saturated sodium bicarbonate. Aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with sodium bicarbonate solution, brine and dried over sodium sulphate. Concentration under reduced pressure and purification by silica gel column chromatography using 20% ethyl acetate: hexane as eluent furnished title compounds Isomer A and B (0.24 g) as a colorless liquid. Yield: 40%

Workup

  1. customreaction
  2. stirringcontinued stirring at about 65° C. for about 8 hours
  3. customCompletion of reaction
  4. customquenched with saturated sodium bicarbonate
  5. extractionAqueous layer was extracted with ethyl acetate
  6. washthe combined organic layers were washed with sodium bicarbonate solution, brine
  7. dry with materialdried over sodium sulphate
  8. concentrationConcentration
  9. customunder reduced pressure and purification by silica gel column chromatography
  10. customhexane as eluent furnished title compounds Isomer A and B (0.24 g) as a colorless liquid

Sources & evidence

ORD record
ord-cf48125b799547deb4f3b1f7b1c45ca6
Source dataset
uspto-grants-2012_07
Patent number
US08227431B2

Reaction notes

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