Trifluoroacetic acid → HCID 18394988, compound

HRID 1602963Notes

Reaction equation

HRID 1602963 reaction equation
O[C:2]([C:15]1[C:16](=[O:52])[NH:17][C:18](=[O:51])[N:19]([CH:50]=1)[C@@H:20]1[O:49][C@H:39]([CH2:40][O:41][Si:42]([C:45]([CH3:48])([CH3:47])[CH3:46])([CH3:44])[CH3:43])[C@@H:30]([O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[C@H:21]1[O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[C:3]1([CH:2]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:15]2[C:16](=[O:52])[NH:17][C:18](=[O:51])[N:19]([CH:50]=2)[C@@H:20]2[O:49][C@H:39]([CH2:40][O:41][Si:42]([C:45]([CH3:46])([CH3:47])[CH3:48])([CH3:44])[CH3:43])[C@@H:30]([O:31][Si:32]([C:35]([CH3:37])([CH3:36])[CH3:38])([CH3:34])[CH3:33])[C@H:21]2[O:22][Si:23]([C:26]([CH3:27])([CH3:28])[CH3:29])([CH3:24])[CH3:25])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 18394995HCID 18394995, compound

Product 1

HCID 18394988HCID 18394988, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of Example 1 step (i), (5-(hydroxy-(1,1-diphenyl)methyl)-2',3',5'-tris-O-((1,1-dimethylethyl)dimethylsilyl)uridine) (6.8 g), was dissolved in dichloromethane (80 ml) and triethylsilane (1.83 ml) and treated with trifluoroacetic acid (1.38 ml). After stirring for 20 minutes the solvents were removed under reduced pressure and any remaining traces removed by azeotroping three times with toluene. The remaining residue was dissolved in dimethylformamide (5 ml) and treated with imidazole (0.54 g) and t-butyldimethylsilylchloride (0.6 g). After stirring for 16 hours the mixture was partitioned between water and iso-hexane and the organic phase was washed with water, collected and dried over magnesium sulphate. The solvent was removed under reduced pressure and the residue was purified by flash silica-gel chromatography eluting with ethyl acetate/iso-hexane mixtures to afford 5-diphenylmethyl-2',3',5'-tris-O-((1,1-dimethylethyl)dimethylsilyl)uridine as a colourless foam (5.94 g).

Workup

  1. customwere removed under reduced pressure
  2. customany remaining traces removed
  3. customby azeotroping three times with toluene
  4. dissolutionThe remaining residue was dissolved in dimethylformamide (5 ml)
  5. additiontreated with imidazole (0.54 g) and t-butyldimethylsilylchloride (0.6 g)
  6. stirringAfter stirring for 16 hours the mixture
  7. customwas partitioned between water and iso-hexane
  8. washthe organic phase was washed with water
  9. customcollected
  10. dry with materialdried over magnesium sulphate
  11. customThe solvent was removed under reduced pressure
  12. customthe residue was purified by flash silica-gel chromatography
  13. washeluting with ethyl acetate/iso-hexane

Sources & evidence

ORD record
ord-2d0819e3bedc4c3abcdcb3766032212b
Source dataset
uspto-grants-1999_11
Patent number
US05985849

Reaction notes

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